Sodium Hydroxide → HCID 178524472, compound

HRID 1914634Notes

Reaction equation

HRID 1914634 reaction equation
C[O:2][C:3](=[O:32])[C:4]1[CH:9]=[CH:8][C:7]([NH:10][CH2:11][C@H:12]2[CH2:17][CH2:16][C@H:15]([NH:18][C:19](=[O:31])[C:20]3[CH:25]=[C:24]([C:26]([F:29])([F:28])[F:27])[CH:23]=[CH:22][C:21]=3[Cl:30])[CH2:14][CH2:13]2)=[N:6][CH:5]=1.[OH-].[Na+]>CO>[Cl:30][C:21]1[CH:22]=[CH:23][C:24]([C:26]([F:29])([F:27])[F:28])=[CH:25][C:20]=1[C:19]([NH:18][C@H:15]1[CH2:16][CH2:17][C@H:12]([CH2:11][NH:10][C:7]2[CH:8]=[CH:9][C:4]([C:3]([OH:32])=[O:2])=[CH:5][N:6]=2)[CH2:13][CH2:14]1)=[O:31]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 178498150HCID 178498150, compound

Product 1

HCID 178524472HCID 178524472, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Trans-6-{[4-(2-Chloro-5-trifluoromethyl-benzoylamino)-cyclohexylmethyl]-amino}-nicotinic acid methyl ester (Example 19.15) (30 mg, 0.06 mmol) is placed in a vial with MeOH (2 mL). 1M NaOH (1 mL) is added and the reaction mixture is stirred at RT for 3 days. The reaction mixture is acidified and the resulting precipitate in the aqueous layer which was filtered and dried to afford the title compound. [MH+456.31], NMR: δH (400 MHz, DMSO); 12.29 (1H, s), 8.53 (1H, d), 8.48 (1H, d), 7.78 (4H, m) 7.35 (1H, m), 6.50 (1H, d), 3.71 (1H, m), 3.19 (2H, m), 1.96 (2H, m), 1.83 (2H, m), 1.52 (1H, m), 1.23 (2H, m), 1.08 (2H, m).

Workup

  1. filtrationthe resulting precipitate in the aqueous layer which was filtered
  2. customdried

Sources & evidence

ORD record
ord-8662fcf78ab746edbfb705e93b192b61
Source dataset
uspto-grants-2013_12
Patent number
US08614213B2

Reaction notes

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