1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → HCID 10197057, compound

HRID 458438

Reaction equation

HRID 458438 reaction equation
[F:1][C:2]1[CH:37]=[C:36]([F:38])[CH:35]=[CH:34][C:3]=1[CH2:4][C:5]1[C:6]([NH:27][C:28](=[O:33])[C:29]([F:32])([F:31])[F:30])=[C:7]([C:18]2[CH:26]=[CH:25][C:21]([C:22]([OH:24])=O)=[CH:20][CH:19]=2)[C:8]2[C:15](=[O:16])[N:14]3[C@@H:10]([CH2:11][CH2:12][CH2:13]3)[C:9]=2[N:17]=1.Cl.CN(C)CCCN=C=NCC.O.ON1C2C=CC=CC=2N=N1.[NH2:62][C@H:63]1[C:71]2[C:66](=[CH:67][CH:68]=[CH:69][CH:70]=2)[CH2:65][CH2:64]1>ClCCl>[F:1][C:2]1[CH:37]=[C:36]([F:38])[CH:35]=[CH:34][C:3]=1[CH2:4][C:5]1[C:6]([NH:27][C:28](=[O:33])[C:29]([F:30])([F:32])[F:31])=[C:7]([C:18]2[CH:26]=[CH:25][C:21]([C:22]([NH:62][C@H:63]3[C:71]4[C:66](=[CH:67][CH:68]=[CH:69][CH:70]=4)[CH2:65][CH2:64]3)=[O:24])=[CH:20][CH:19]=2)[C:8]2[C:15](=[O:16])[N:14]3[C@@H:10]([CH2:11][CH2:12][CH2:13]3)[C:9]=2[N:17]=1

Participants

6

Reactant 4

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 2733933(R)-(-)-1-AminoindanHCID 27960291-Hydroxybenzotriazole hydrateHCID 86598168HCID 86598168, compound

Product 1

HCID 10197057HCID 10197057, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To the 2.0 ml dichloromethane solution containing the acid (G, 4-{(9aS)-2-(2,4-difluorobenzyl)-5-oxo-3-[(trifluoroacetyl)amino]-7,8,9,9a-tetrahydro-5H-pyrido[2,3-a]pyrrolizin-4-yl}benzoic acid, 956 mg, 1.8 mmol), 1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (691 mg, 3.6 mmol) and 1-hydroxybenzotriazole hydrate, 480 mg (R)-(−)-1-aminoindan (3.6 mmol) was added. The resulting mixture was stirred at room temperature for 3 hours. Diluted with dichloromethane. Washed with water and brine subsequently. Dried with sodium sulfate. Upon the removal of the solvent, the residue was purified with flash chromatography. 320 mg of the title compound as a light yellowish solid was obtained. NMR (400 MHz, CDCl3) δ 7.95 (m, 2H), 7.32 (m, 5H), 6.95 (m, 4 m), 5.62 (m, 1H), 4.59 (m, 1H), 4.15 (m, 1H), 3.55 (s, 2H), 3.15 (m, 1H), 3.06 (m, 1H), 2.90 (m, 1H), 2.58 (m, 1H), 2.32 (m, 2H), 2.02 (m, 1H), 1.25 (m, 1H) ppm. ESI-MS m/z 647 (M+H)+, 645 (M−H)−.

Workup

  1. additionwas added
  2. washWashed with water and brine subsequently
  3. dry with materialDried with sodium sulfate
  4. customUpon the removal of the solvent
  5. customthe residue was purified with flash chromatography

Sources & evidence

ORD record
ord-0e756a8032e844ee920778b955b87f2c
Source dataset
uspto-grants-2007_03
Patent number
US07189851B2

Linked notes

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