Ammonia → HCID 53357228, compound

HRID 1807320Notes

Reaction equation

HRID 1807320 reaction equation
[Cl:1][C:2]1[C:3]([F:41])=[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]([OH:37])=O)=[CH:33][C:32]=2[F:40])=[O:29])[CH:5]=[CH:6][CH:7]=1.CC[N:44](C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.N>CO.C(Cl)Cl>[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:41])[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]([CH3:26])([CH3:25])[CH3:27])[NH:10]2)=[O:29])=[C:32]([F:40])[CH:33]=1)(=[O:37])[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 53358688HCID 53358688, compound

Product 1

HCID 53357228HCID 53357228, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

In a 10 mL round-bottomed flask, 4-((2R,3S,4R,5S)-3-(3-chloro-2-fluorophenyl)-4-(4-chloro-2-fluorophenyl)-4-cyano-5-neopentylpyrrolidine-2-carboxamido)-3-fluorobenzoic acid (70 mg, 116 μmol, Eq: 1.00) was combined with CH2Cl2 (5.43 ml) to give a suspension. DIPEA (18.0 mg, 24.3 μl, 139 μmol, Eq: 1.2) and HATU (48.4 mg, 127 μmol, Eq: 1.1) were added. The reaction was stirred for 2 minutes and 2M ammonia (290 μl, 579 μmol, Eq: 5) in Methanol was added. The reaction mixture was stirred for overnight.

Workup

  1. customto give a suspension
  2. stirringThe reaction mixture was stirred for overnight

Sources & evidence

ORD record
ord-323cdfb9e45e455eb8c930c922e33e14
Source dataset
uspto-grants-2013_01
Patent number
US08354444B2

Reaction notes

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