Ammonium Hydroxide → HCID 86586071, compound

HRID 887527Notes

Reaction equation

HRID 887527 reaction equation
[Cl:1][C:2]1[C:7]([C:8]([NH:10][C:11]2[CH:12]=[CH:13][C:14]([C:29]([F:35])([F:34])[C:30]([F:33])([F:32])[F:31])=[C:15]([CH:28]=2)[O:16][CH2:17][CH:18]([O:24]C(=O)C)[N:19]2[CH2:23][CH2:22][CH2:21][CH2:20]2)=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1.[NH4+].[OH-]>CO>[Cl:1][C:2]1[N:3]=[CH:4][CH:5]=[CH:6][C:7]=1[C:8]([NH:10][C:11]1[CH:12]=[CH:13][C:14]([C:29]([F:35])([F:34])[C:30]([F:32])([F:33])[F:31])=[C:15]([O:16][CH2:17][C@@H:18]([OH:24])[N:19]2[CH2:20][CH2:21][CH2:22][CH2:23]2)[CH:28]=1)=[O:9]

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 86586072HCID 86586072, compound

Product 1

HCID 86586071HCID 86586071, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Acetic acid 2-{5-[(2-chloro-pyridine-3-carbonyl)-amino]-2-pentafluoroethyl-phenoxy}-1-pyrrolidin-1-yl-ethyl ester (408 mg) was dissolved in MeOH (15 ml) and NH4OH (6 ml) was added and the mixture was stirred at RT for 6 h. The reaction was concentrated in vacuo and dried under high vacuum. The residue was purified over silica gel column (8:92:0.6 MeOH:CH2Cl2:NH4OH). The purified fractions were concentrated in vacuo and dried again to provide (R)-2-chloro-N-[3-(2-hydroxy-2-pyrrolidin-1-yl-ethoxy)-4-pentafluoroethyl-phenyl]-nicotinamide as a white foam.

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. customdried under high vacuum
  3. customThe residue was purified over silica gel column (8:92:0.6 MeOH:CH2Cl2:NH4OH)
  4. concentrationThe purified fractions were concentrated in vacuo
  5. customdried again

Sources & evidence

ORD record
ord-3e12820e746e465eaabafafbf243e4be
Source dataset
uspto-grants-2012_08
Patent number
US08247430B2

Reaction notes

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