Ammonium Hydroxide → HCID 11656677, compound

HRID 1994142Notes

Reaction equation

HRID 1994142 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:35])[CH2:10][CH2:11][C:12]2[CH:13]=[C:14]([CH:32]=[CH:33][CH:34]=2)[O:15][C:16]2[CH:21]=[CH:20][N:19]=[C:18]([C:22]3[O:26][C:25]([C:27]([O:29]CC)=O)=[N:24][N:23]=3)[CH:17]=2)=[CH:4][C:3]=1[C:36]([F:39])([F:38])[F:37].[NH4+:40].[OH-]>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:35])[CH2:10][CH2:11][C:12]2[CH:13]=[C:14]([CH:32]=[CH:33][CH:34]=2)[O:15][C:16]2[CH:21]=[CH:20][N:19]=[C:18]([C:22]3[O:26][C:25]([C:27]([NH2:40])=[O:29])=[N:24][N:23]=3)[CH:17]=2)=[CH:4][C:3]=1[C:36]([F:38])([F:37])[F:39]

Participants

3

Reactant 2

HCID 14923Ammonium HydroxideHCID 58674465HCID 58674465, compound

Product 1

HCID 11656677HCID 11656677, compound

Procedure

A solution of ethyl 5-{4-[3-(3-{[4-chloro-3-(trifluoromethyl)phenyl]-amino}-3-oxopropyl)phenoxy]pyridin-2-yl}-1,3,4-oxadiazole-2-carboxylate (100 mg) in NH4OH (10 mL) was allowed to stir at rt for 90 min. The reaction mixture was concentrated and the residue recrystallized from MeOH to give A-102. 1H NMR (300 MHz, d6-DMSO) δ: 8.70 (br s, 1H), 8.62 (d, 1H), 8.29 (br s, 1H), 8.13 (d, 1H), 7.76 (dd, 1H), 7.58-7.64 (m, 2H), 7.45 (t, 1H), 7.23-7.28 (m, 1H), 7.14-7.19 (m, 2H), 7.07-7.13 (m, 1H), 2.97 (t, 2H), and 2.69 (t, 2H). LCMS, FA: Rt=1.77 min, [MH+ 532.1].

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue recrystallized from MeOH
  3. customto give A-102

Sources & evidence

ORD record
ord-c4fc8005adef4f4992ee6d481b8845f5
Source dataset
uspto-grants-2010_01
Patent number
US07652041B2

Reaction notes

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