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1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → HCID 178470590, compound

HRID 989524
Notes
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Reaction equation

HRID 989524 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH:11]([C:17]1[NH:18][CH:19]=[C:20]([N+:22]([O-])=O)[N:21]=1)[C:12]([O:14][CH2:15][CH3:16])=[O:13].Cl.CN(C)CCCN=C=NCC.[C:37]([O:41][C:42]([NH:44][C:45]([CH3:64])([CH3:63])[C:46]([NH:48][C@H:49]([CH2:53][C:54]1[C:62]2[C:57](=[CH:58][CH:59]=[CH:60][CH:61]=2)[NH:56][CH:55]=1)[C:50](O)=[O:51])=[O:47])=[O:43])([CH3:40])([CH3:39])[CH3:38]>[Pd].O1CCCC1>[C:37]([O:41][C:42]([NH:44][C:45]([CH3:64])([CH3:63])[C:46]([NH:48][C@H:49]([CH2:53][C:54]1[C:62]2[C:57](=[CH:58][CH:59]=[CH:60][CH:61]=2)[NH:56][CH:55]=1)[C:50]([NH:22][C:20]1[N:21]=[C:17]([CH:11]([C:2]2[CH:3]=[CH:4][C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[CH:1]=2)[C:12]([O:14][CH2:15][CH3:16])=[O:13])[NH:18][CH:19]=1)=[O:51])=[O:47])=[O:43])([CH3:40])([CH3:38])[CH3:39]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 15895387(R)-2-(2-((tert-Butoxycarbonyl)amino)-2-methylpropanamido)-3-(1H-indol-3-yl)propanoic acidHCID 178470591HCID 178470591, compound

Product 1

HCID 178470590HCID 178470590, compoundYield 41.1%

Reagents, catalysts & solvents 2

HCID 23938
Palladium
Catalyst
HCID 8028TetrahydrofuranSolvent2×

Procedure

A mixture of ethyl 2-(2-naphthyl)-2-(4-nitroimidazolyl)acetate (2.04 grams, 6.27 mmol), tetrahydrofuran (20 mL), and 10% palladium on carbon (2.04 gram) was hydrogenated at ambient temperature and pressure until complete as determined by hplc (20 hours). The catalyst was removed by filtration and rinsed with tetrahydrofuran (10 mL). The filtrate was added to a slurry consisting of 1-[3-(dimethylamino)propyl-3-ethylcarbodiimide hydrochloride (1.20 grams, 6.27 mmol), tetrahydrofuran (10 mL), and (2R)-2-{2-[(tert-butoxy)carbonylamino]-2-methylpropanoylamino}-3-indol-3-ylpropanoic acid (2.44 grams, 6.27 mmol) and stirred 16 hours at ambient temperature. The reaction mixture was partitioned between water (150 mL) and ethyl acetate (3×50 mL). The organic extracts were combined, washed with saturated sodium chloride solution, dried using sodium sulfate, and evaporated. The resulting crude oil was purified by column chromatography on silica gel with hexane:ethyl acetate:methanol (10:10:1) as an eluent giving 1.72 grams (41%) of ethyl 2-(4-((2R)-2-{2-[(tert-butoxy)carbonylamino]-2-methylpropanoylamino}-3-indol-3-ylpropanoyl amino)imidazolyl]-2-(2-naphthyl)acetate. A 0.2 gram sample was further purified using preparative reverse phase hplc to give 0.16 grams of ethyl 2-[4-((2R)-2-{2-[(tert-butoxy)carbonylamino]-2-methylpropanoylamino)-3-indol-3-ylpropanoyl amino)imidazolyl]-2-(2-naphthyl)acetate for analytical study. MS (FIA) m/z 667.4 [(M+H)+]. Anal. calcd. exact mass for C37H43N6O6 [(M+H)+]=667.3244. Exact mass found by mass spectrometry: C37H43N6O6 [(M+H)+]=667.3254. 1H nmr (CDCl3): 1.25-1.42 (m, 19H), 3.24-3.33 (m, 2H), 4.28-4.33 (m, 2H), 4.98-5.01 (m, 1H), 5.94 (s, 1H), 6.85-7.01(m, 3H), 7.18-7.21 (m, 2H), 7.35-7.39 (m, 2H), 7.49-7.58 (m, 4H), 7.78-7.84 (m, 4H), 8.69 (s, 1H), 10.65 (s, broad, 1H).

Workup

  1. customwas hydrogenated at ambient temperature
  2. customas determined by hplc (20 hours)
  3. customThe catalyst was removed by filtration
  4. washrinsed with tetrahydrofuran (10 mL)
  5. additionThe filtrate was added to a slurry
  6. customThe reaction mixture was partitioned between water (150 mL) and ethyl acetate (3×50 mL)
  7. washwashed with saturated sodium chloride solution
  8. customdried
  9. customevaporated
  10. customThe resulting crude oil was purified by column chromatography on silica gel with hexane:ethyl acetate:methanol (10:10:1) as an eluent

Sources & evidence

ORD record
ord-be717364c8084c5689ef4f51998da9a3
Source dataset
uspto-grants-2003_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06639076B1

Reaction notes

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