Hydrochloric Acid → HCID 57899074, compound

HRID 1404278Notes

Reaction equation

HRID 1404278 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, 2 H) 1.3 (s, 1 H) 1.6 (s, 2 H) 1.9 (s, 6 H) 3.5 (s, 6 H) 7.4 (s, 2 H) 7.9 (s, 1 H) 8.0 (s, 2 H) 8.6 (s, 1 H), 8.6 (s, 1 H) 8.9 (s, 1 H) 9.1 (s, 1 H) 10.9 (s, 1 H); (M+H)+ 457.1.

Workup

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

Sources & evidence

ORD record
ord-ee110c92b5c34ea7a9e54e50abc41d90
Source dataset
uspto-grants-2014_12
Patent number
US08912208B2

Reaction notes

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