Diisopropylethylamine → HCID 57818278, compound

HRID 1511474Notes

Reaction equation

HRID 1511474 reaction equation
[C:1]([NH:5][C:6](=[O:39])[NH:7][C@@H:8]([C:35]([CH3:38])([CH3:37])[CH3:36])[C:9]([N:11]1[CH2:15][C@H:14]([O:16][C:17]2[C:18]3[CH:31]=[CH:30][S:29][C:19]=3[N:20]=[C:21]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=3)[N:22]=2)[CH2:13][C@H:12]1[C:32](O)=[O:33])=[O:10])([CH3:4])([CH3:3])[CH3:2].[NH2:40][C@@H:41]([CH2:50][CH2:51][CH3:52])[CH:42]([OH:49])[C:43]([NH:45][CH:46]1[CH2:48][CH2:47]1)=[O:44].F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.C(N(C(C)C)CC)(C)C>ClCCl.CN(C)C=O>[C:1]([NH:5][C:6](=[O:39])[NH:7][C@@H:8]([C:35]([CH3:37])([CH3:38])[CH3:36])[C:9]([N:11]1[CH2:15][C@H:14]([O:16][C:17]2[C:18]3[CH:31]=[CH:30][S:29][C:19]=3[N:20]=[C:21]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=3)[N:22]=2)[CH2:13][C@H:12]1[C:32]([NH:40][C@@H:41]([CH2:50][CH2:51][CH3:52])[CH:42]([OH:49])[C:43]([NH:45][CH:46]1[CH2:47][CH2:48]1)=[O:44])=[O:33])=[O:10])([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 23634853(3S)-3-Amino-N-cyclopropyl-2-hydroxyhexanamideHCID 57818334HCID 57818334, compound

Product 1

HCID 57818278HCID 57818278, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

(2S,4R)-1-((S)-2-(3-tert-butylureido)-3,3-dimethylbutanoyl)-4-(2-(pyridin-2-yl)thieno[2,3-d]pyrimidin-4-yloxy)pyrrolidine-2-carboxylic acid (60) (1 mmol) was coupled with (3S)-3-amino-N-cyclopropyl-2-hydroxyhexanamide (1 mmol, as prepared in Reference A) in the presence of O (7 azabenzotriazol 1 yl) 1,1,3,3 tetramethyl-uronium hexafluorophosphate (HATU) (1.2 mmol) and diisopropylethylamine (4 mmol) in dichloromethane and N,N-dimethylformamide to give (2S,4R)-1-((S)-2-(3-tert-butylureido)-3,3-dimethylbutanoyl)-N-((3S)-1-(cyclopropylamino)-2-hydroxy-1-oxohexan-3-yl)-4-(2-(pyridin-2-yl)thieno[2,3-d]pyrimidin-4-yloxy)pyrrolidine-2-carboxamide (61) as a crude solid after aqueous/organic extractive work up.

Sources & evidence

ORD record
ord-bd90e02a851648878551ee45e9fc99f3
Source dataset
uspto-grants-2012_07
Patent number
US08211897B2

Reaction notes

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