Hydrochloric Acid → HCID 24937519, compound

HRID 1404226Notes

Reaction equation

HRID 1404226 reaction equation
C([O:3][C:4](=[O:32])[CH2:5][CH:6]1[CH2:11][CH2:10][CH:9]([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[N:19]=[C:20]([NH:23][C:24]4[CH:29]=[CH:28][CH:27]=[C:26]([O:30][CH3:31])[CH:25]=4)[S:21][CH:22]=3)=[CH:14][CH:13]=2)[CH2:8][CH2:7]1)C.[Li+].[OH-].Cl>>[CH3:31][O:30][C:26]1[CH:25]=[C:24]([NH:23][C:20]2[S:21][CH:22]=[C:18]([C:15]3[CH:16]=[CH:17][C:12]([CH:9]4[CH2:8][CH2:7][CH:6]([CH2:5][C:4]([OH:32])=[O:3])[CH2:11][CH2:10]4)=[CH:13][CH:14]=3)[N:19]=2)[CH:29]=[CH:28][CH:27]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 86634686HCID 86634686, compound

Product 1

HCID 24937519HCID 24937519, compound

Conditions

Temperature
50 °C

Procedure

To the reaction mixture of (4-{4-[2-(3-methoxyphenylamino)-thiazol-4-yl]-phenyl}-cyclohexyl)-acetic acid ethyl ester from step B is added LiOH (10% solution, 1 mL). It is then heated at 50° C. for 18 h. The mixture is then acidified with HCl solution (1 N) to pH=5. The resulting solid is filtered and dried under high vacuum to give the title compound (26.8 mg) as a solid; 1H NMR (400 MHz, DMSO-d6) δ ppm 0.96-1.07 (m, 2 H) 1.31-1.43 (m, 2 H) 1.50-1.52 (m, 1 H) 1.58-1.64 (m, 1 H) 1.71 (d, J=9.60 Hz, 4 H) 2.03 (d, J=6.57 Hz, 2 H) 2.27 (br. s., 1 H) 3.67 (s, 3 H) 6.43 (dd, J=7.83, 1.77 Hz, 1 H) 7.03 (dd, J=7.20, 0.88 Hz, 1 H) 7.09-7.20 (m, 4 H) 7.44 (br. s., 1 H) 7.70 (d, J=8.08 Hz, 2 H) 10.13 (br. s., 1 H); MS (M+H)+=423.2.

Workup

  1. filtrationThe resulting solid is filtered
  2. customdried under high vacuum

Sources & evidence

ORD record
ord-aa458afc3a3f49c783b5c872d010c1dc
Source dataset
uspto-grants-2014_12
Patent number
US08912208B2

Reaction notes

Loading…