Ammonium Chloride → HCID 75631837, compound

HRID 909092Notes

Reaction equation

HRID 909092 reaction equation
[Cl:1][C:2]1[C:3]([F:36])=[C:4]([C@@H:8]2[C@:12]([C:15]3[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=3[F:22])([C:13]#[N:14])[C@H:11]([CH2:23][C:24]([CH3:27])([CH3:26])[CH3:25])[CH2:10][N:9]2[C:28]([NH:30][CH2:31][CH2:32][C:33](O)=[O:34])=[O:29])[CH:5]=[CH:6][CH:7]=1.CC[N:39](C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[Cl-].[NH4+]>CN(C=O)C>[C:33]([CH2:32][CH2:31][NH:30][C:28]([N:9]1[CH2:10][CH:11]([CH2:23][C:24]([CH3:25])([CH3:26])[CH3:27])[C:12]([C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=2[F:22])([C:13]#[N:14])[CH:8]1[C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[C:3]=1[F:36])=[O:29])(=[O:34])[NH2:39]

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 51357253HCID 51357253, compound

Product 1

HCID 75631837HCID 75631837, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In a manner similar to the method described in Example 63, a mixture of rac-3-{[(2S,3S,4S)-2-(3-chloro-2-fluoro-phenyl)-3-(4-chloro-2-fluoro-phenyl)-3-cyano-4-(2,2-dimethyl-propyl)-pyrrolidine-1-carbonyl]-amino}-propionic acid (25 mg, 0.0464 mmole, example 73), DIPEA (42 mg, 0.324 mmol) and HATU (26.4 mg, 0.069 mmol) in DMF was reacted with ammonium chloride (6.2 mg, 0.11 mmol) to give rac-(2S,3S,4S)-2-(3-chloro-2-fluoro-phenyl)-3-(4-chloro-2-fluoro-phenyl)-3-cyano-4-(2,2-dimethyl-propyl)-pyrrolidine-1-carboxylic acid (2-carbamoyl-ethyl)-amide (14.1 mg, 57%). HRMS (ES+) m/z Calcd for C26H28Cl2F2N4O2+H [(M+H)+]: 537.1630; Found: 537.1630.

Sources & evidence

ORD record
ord-243e3b2a79a243e7a707b0b058d57968
Source dataset
uspto-grants-2011_09
Patent number
US08017607B2

Reaction notes

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