Ammonia → HCID 53357372, compound

HRID 1807324Notes

Reaction equation

HRID 1807324 reaction equation
[Cl:1][C:2]1[C:3]([F:42])=[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])[NH:10][C@H:9]2[C:28]([NH:30][C:31]2[CH:39]=[CH:38][C:34]([C:35](O)=[O:36])=[C:33]([O:40][CH3:41])[CH:32]=2)=[O:29])[CH:5]=[CH:6][CH:7]=1.C[N:44](C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.N>C(Cl)Cl.CO>[C:35]([C:34]1[CH:38]=[CH:39][C:31]([NH:30][C:28]([C@H:9]2[C@H:8]([C:4]3[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[C:3]=3[F:42])[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]([CH3:25])([CH3:26])[CH3:27])[NH:10]2)=[O:29])=[CH:32][C:33]=1[O:40][CH3:41])(=[O:36])[NH2:44]

Participants

7

Reactant 4

HCID 222AmmoniaHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 59249270HCID 59249270, compound

Product 1

HCID 53357372HCID 53357372, compoundYield 91.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 4-((2R,3S,4R,5S)-3-(3-chloro-2-fluorophenyl)-4-(4-chloro-2-fluorophenyl)-4-cyano-5-neopentylpyrrolidine-2-carboxamido)-2-methoxybenzoic acid (250 mg, 0.41 mmol) in methylene chloride (8 ml), HATU (154 mg, 0.41 mmol) and DIPEA (0.1 ml, 0.57 mmol) were added. The mixture was stirred for 5 min. at rt and ammonia in methanol (2N, 2 ml) was added and the mixture was stirred overnight. The solvent was reduced to 3 ml and loaded onto a silica gel column, eluted with 3% methanol and methylene chloride to give 230 mg desired product. (ES+) m/z Calcd: [(M+H)+]: 615. found: 615.

Workup

  1. stirringthe mixture was stirred overnight
  2. washeluted with 3% methanol and methylene chloride

Sources & evidence

ORD record
ord-eae4ea4fcd024052b39f7a7345b99e42
Source dataset
uspto-grants-2013_01
Patent number
US08354444B2

Reaction notes

Loading…