Hydrochloric Acid → HCID 57899074, compound

HRID 76084Notes

Reaction equation

HRID 76084 reaction equation
C[O:2][C:3](=[O:34])[CH2:4][CH:5]1[CH2:10][CH2:9][CH:8]([C:11]2[CH:16]=[CH:15][C:14]([C:17]3[CH:22]=[N:21][C:20]([NH:23][C:24]4[CH:25]=[N:26][C:27]([C:30]([F:33])([F:32])[F:31])=[CH:28][CH:29]=4)=[CH:19][N:18]=3)=[CH:13][CH:12]=2)[CH2:7][CH2:6]1.[OH-].[Li+].Cl>C1COCC1.O>[F:33][C:30]([F:31])([F:32])[C:27]1[N:26]=[CH:25][C:24]([NH:23][C:20]2[N:21]=[CH:22][C:17]([C:14]3[CH:13]=[CH:12][C:11]([CH:8]4[CH2:7][CH2:6][CH:5]([CH2:4][C:3]([OH:34])=[O:2])[CH2:10][CH2:9]4)=[CH:16][CH:15]=3)=[N:18][CH:19]=2)=[CH:29][CH:28]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 66615921(4-{4-[5-(6-Trifluoromethyl-pyridin-3-ylamino)-pyrazin-2-yl]-phenyl}-cyclohexyl)-acetic acid methyl ester

Product 1

HCID 57899074HCID 57899074, compound

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

To a solution of (4-{4-[5-(6-trifluoromethyl-pyridin-3-ylamino)-pyrazin-2-yl]-phenyl}-cyclohexyl)-acetic acid methyl ester (0.051 g) in 4 Ml THF/water (1:1) was added solid lithium hydroxide (0.030 g). The reaction was stirred at room temperature for 48 h. then heated to 45° C. for 24 h. The reaction was neutralized with 6 N hydrochloric acid and then purified by reverse-phase preparative HPLC to afford the title compound: 1H NMR (400 MHz, DMSO-D6) δ ppm 1.1 (s, 2H) 1.3 (s, 1H) 1.6 (s, 2H) 1.9 (s, 6H) 3.5 (s, 6H) 7.4 (s, 2H) 7.9 (s, 1H) 8.0 (s, 2H) 8.6 (s, 1H), 8.6 (s, 1H) 8.9 (s, 1H) 9.1 (s, 1H) 10.9 (s, 1H); (M+H)+457.1.

Workup

  1. temperaturethen heated to 45° C. for 24 h
  2. custompurified by reverse-phase preparative HPLC

Sources & evidence

ORD record
ord-cae34a86418f453b9b6814173e08bd39
Source dataset
uspto-grants-2014_09
Patent number
US08835451B2

Reaction notes

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