Cyclopropanecarboxylic acid → HCID 178523889, compound

HRID 2273046Notes

Reaction equation

HRID 2273046 reaction equation
[NH2:1][C@H:2]([C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)[C:3]([N:5]1[CH2:9][CH2:8][CH2:7][C@H:6]1[C:10]([NH:12][CH:13]1[CH2:16][CH:15]([C:17]2[CH:22]=[CH:21][C:20]([C:23]3[N:24]=[C:25]([C@@H:28]4[CH2:32][CH2:31][CH2:30][N:29]4[C:33](=[O:42])[C@H:34]([NH2:41])[C:35]4[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=4)[NH:26][CH:27]=3)=[CH:19][CH:18]=2)[CH2:14]1)=[O:11])=[O:4].[CH:49]1([C:52]([OH:54])=O)[CH2:51][CH2:50]1.CCN([CH:61]([CH3:63])[CH3:62])C(C)C.CN([C:67]([O:71]N1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>ClCCl>[CH:49]1([C:52]([NH:1][C@H:2]([C:43]2[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=2)[C:3]([N:5]2[CH2:9][CH2:8][CH2:7][C@H:6]2[C:10]([NH:12][CH:13]2[CH2:14][CH:15]([C:17]3[CH:18]=[CH:19][C:20]([C:23]4[N:24]=[C:25]([C@@H:28]5[CH2:32][CH2:31][CH2:30][N:29]5[C:33](=[O:42])[C@H:34]([NH:41][C:67]([CH:61]5[CH2:63][CH2:62]5)=[O:71])[C:35]5[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=5)[NH:26][CH:27]=4)=[CH:21][CH:22]=3)[CH2:16]2)=[O:11])=[O:4])=[O:54])[CH2:51][CH2:50]1

Participants

6

Reactant 4

HCID 15655Cyclopropanecarboxylic acidHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 178511837HCID 178511837, compound

Product 1

HCID 178523889HCID 178523889, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (S)-1-((R)-2-amino-2-phenylacetyl)-N-(3-(4-(2-((S)-1-((R)-2-amino-2-phenylacetyl)pyrrolidin-2-yl)-1H-imidazol-4-yl)phenyl)cyclobutyl)pyrrolidine-2-carboxamide (80 mg, 0.124 mmol) in dichloromethane (20 mL), cyclopropyl carboxylic acid (22 mg, 0.26 mmol), DIPEA (0.5 mL) and HATU (94 mg, 0.26 mmol) were added at rt. After stirring overnight, the reaction was washed with brine and H2O, dried with Na2SO4. After removal of the solvent, the crude product was purified by silica gel column chromatography (DCM/MeOH=10/1 (v/v)) to afford (S)-1-((R)-2-(cyclopropanecarboxamido)-2-phenylacetyl)-N-(3-(4-(2-((S)-1-((R)-2-(cyclopropanecarboxamido)-2-phenylacetyl)pyrrolidin-2-yl)-1H-imidazol-4-yl)phenyl)cyclobutyl)pyrrolidine-2-carboxamide (A14) (25 mg).

Workup

  1. washthe reaction was washed with brine and H2O
  2. dry with materialdried with Na2SO4
  3. customAfter removal of the solvent
  4. customthe crude product was purified by silica gel column chromatography (DCM/MeOH=10/1 (v/v))

Sources & evidence

ORD record
ord-6adaf72e3986419c83b18643869631f8
Source dataset
uspto-grants-2015_09
Patent number
US09120779B2

Reaction notes

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