Dichloromethane → HCID 178428315, compound

HRID 410548Notes

Reaction equation

HRID 410548 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([C:19]2[S:23][C:22]([CH:24]3[CH2:29][CH2:28][CH:27]([C:30]([O:32]CC)=[O:31])[CH2:26][CH2:25]3)=[N:21][CH:20]=2)[CH:5]=[C:6]([NH:8][C:9]2[N:14]=[C:13]([C:15]([F:18])([F:17])[F:16])[CH:12]=[CH:11][N:10]=2)[CH:7]=1.[OH-].[K+].[Cl:37]CCl>O1CCCC1>[Cl-:37].[C:30]([CH:27]1[CH2:26][CH2:25][CH:24]([C:22]2[S:23][C:19]([C:4]3[CH:5]=[C:6]([NH:8][C:9]4[N:14]=[C:13]([C:15]([F:17])([F:18])[F:16])[CH:12]=[CH:11][NH+:10]=4)[CH:7]=[C:2]([CH3:1])[CH:3]=3)=[CH:20][N:21]=2)[CH2:29][CH2:28]1)([OH:32])=[O:31]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 14797Potassium HydroxideHCID 58456402HCID 58456402, compound

Product 1

HCID 178428315HCID 178428315, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To ethyl 4-[5-(3-methyl-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)-1,3-thiazol-2-yl]cyclohexanecarboxylate (0.60 g, 0.12 mmol) in tetrahydrofuran (0.61 mL) was added potassium hydroxide (1.2 mL, 1 M in methanol) and the reaction was stirred overnight at room temperature. Upon completion, the reaction was diluted with dichloromethane and washed twice with hydrochloric acid (2 M in water). The organic layer was dried under reduced pressure to give 2-({3-[2-(4-carboxycyclohexyl)-1,3-thiazol-5-yl]-5-methylphenyl}amino)-4-(trifluoromethyl)pyrimidin-1-ium chloride (0.060 g, 85% yield). MS ESI: [M+H]+ m/z 463.1. 1H NMR (500 MHz, DMSO-d6) δ 10.25 (s, 1H), 8.83 (d, J=5.2, 1H), 8.06-7.81 (m, 2H), 7.44 (s, 1H), 7.27 (d, J=5.8, 1H), 7.14 (s, 1H), 2.30 (s, 3H), 2.14-2.04 (m, 110, 2.03-1.83 (m, 4H), 1.82-1.61 (m, 3H), 1.55-1.33 (m, 2H). rhSYK activity=+++

Workup

  1. washwashed twice with hydrochloric acid (2 M in water)
  2. customThe organic layer was dried under reduced pressure

Sources & evidence

ORD record
ord-aadda2199ba644b0842399a8949715ce
Source dataset
uspto-grants-2014_06
Patent number
US08759366B2

Reaction notes

Loading…