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Triethylamine → HCID 68758997, compound

HRID 79586
Notes
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Reaction equation

HRID 79586 reaction equation
[C:1]([O:5][C:6]([N:8]([CH:21]([CH3:23])[CH3:22])[CH2:9][C@H:10]([C:14]1[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=1)[C:11](O)=[O:12])=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.C(N=C=NCCCN(C)C)C.C1C=CC2N(O)N=NC=2C=1.O.C(N(CC)CC)C.[CH:54]([O:57][C:58]1[C:59]([N:67]2[CH2:72][CH2:71][NH:70][CH2:69][CH2:68]2)=[C:60]2[CH:66]=[CH:65][NH:64][C:61]2=[N:62][CH:63]=1)([CH3:56])[CH3:55]>C(Cl)Cl>[Cl:20][C:17]1[CH:18]=[CH:19][C:14]([C@H:10]([C:11]([N:70]2[CH2:71][CH2:72][N:67]([C:59]3[C:58]([O:57][CH:54]([CH3:56])[CH3:55])=[CH:63][N:62]=[C:61]4[NH:64][CH:65]=[CH:66][C:60]=34)[CH2:68][CH2:69]2)=[O:12])[CH2:9][N:8]([CH:21]([CH3:23])[CH3:22])[C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:4])[CH3:3])=[CH:15][CH:16]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 59564929(2S)-3-[tert-butoxycarbonyl(isopropyl)amino]-2-(4-chlorophenyl)propanoic acidHCID 68760129HCID 68760129, compound

Product 1

HCID 68758997
HCID 68758997, compound
Yield 62%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

(S)-3-(tert-Butoxycarbonyl(isopropyl)amino)-2-(4-chlorophenyl)propanoic acid (59 mg, 0.17 mmol, see Example H), N1-((ethylimino)methylene)-N3,N3-dimethylpropane-1,3-diamine hydrochloride (44 mg, 0.23 mmol), HOBt-H2O (35 mg, 0.23 mmol) and triethylamine (12 mg, 0.12 mmol) were added to 5-isopropoxy-4-(piperazin-1-yl)-1H-pyrrolo[2,3-b]pyridine (30 mg, 0.12 mmol) in DCM (10 mL). The reaction was stirred at room temperature for 18 hours. The reaction was then diluted with DCM (50 mL) and washed with 1N HCL, 10% K2CO3 and brine. After drying over MgSO4, the residue was concentrated to dryness and purified by chromatography (SP4, 12+M, water/ACN 90/10→0/100, 20 CV) to yield (S)-tert-butyl 2-(4-chlorophenyl)-3-(4-(5-isopropoxy-1H-pyrrolo[2,3-b]pyri din-4-yl)piperazin-1-yl)-3-oxopropyl(isopropyl)carbamate (42 mg, 62% yield) as a solid.

Workup

  1. washwashed with 1N HCL, 10% K2CO3 and brine
  2. dry with materialAfter drying over MgSO4
  3. concentrationthe residue was concentrated to dryness
  4. custompurified by chromatography (SP4, 12+M, water/ACN 90/10→0/100, 20 CV)

Sources & evidence

ORD record
ord-f406d72411904f0199c23177fcc05d5e
Source dataset
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08841304B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes