5-(4-Fluorophenyl)-2-methyl-1,3-thiazole-4-carboxylic acid → HCID 49858384, compound

HRID 536598Notes

Reaction equation

HRID 536598 reaction equation
OC1C2N=NNC=2C=CC=1.[F:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[S:22][C:21]([CH3:23])=[N:20][C:19]=2[C:24]([OH:26])=O)=[CH:14][CH:13]=1.[CH2:27]1[C:29]2([CH2:34][CH2:33][NH:32][CH:31]([CH2:35][NH:36][C:37]3[CH:46]=[CH:45][C:44]([Cl:47])=[CH:43][C:38]=3[C:39]([O:41][CH3:42])=[O:40])[CH2:30]2)[CH2:28]1>ClCCl>[Cl:47][C:44]1[CH:45]=[CH:46][C:37]([NH:36][CH2:35][CH:31]2[N:32]([C:24]([C:19]3[N:20]=[C:21]([CH3:23])[S:22][C:18]=3[C:15]3[CH:14]=[CH:13][C:12]([F:11])=[CH:17][CH:16]=3)=[O:26])[CH2:33][CH2:34][C:29]3([CH2:27][CH2:28]3)[CH2:30]2)=[C:38]([CH:43]=1)[C:39]([O:41][CH3:42])=[O:40]

Participants

5

Reactant 3

HCID 223241255-(4-Fluorophenyl)-2-methyl-1,3-thiazole-4-carboxylic acidHCID 66848224HCID 66848224, compound2×HCID 178418300HCID 178418300, compound

Product 1

HCID 49858384HCID 49858384, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of hydroxybenzotriazole (13 mg, 0.097 mmol) and O-(benzotriazol-1-yl)-N,N,N′N′-tetramethyluronium hexafluorophosphate HCl (23 mg, 0.12 mmol) in anhydrous dichloromethane (2 ml), 5-(4-fluorophenyl)-2-methylthiazole-4-carboxylic acid (23 mg, 0.097 mmole) was added and the resulting solution was stirred 1 h at room temperature. (±) methyl 2-(6-azaspiro[2.5]octan-5-ylmethylamino)-5-chlorobenzoate (intermediate 10) (20 mg, 0.08 mmol) was added and the resulting mixture was stirred at the same temperature overnight. The mixture was washed with NaHCO3 saturated solution (3×5 ml).

Workup

  1. stirringthe resulting mixture was stirred at the same temperature overnight
  2. washThe mixture was washed with NaHCO3 saturated solution (3×5 ml)

Sources & evidence

ORD record
ord-a534a35a0a314f07988ddfb3567318d4
Source dataset
uspto-grants-2014_10
Patent number
US08859608B2

Reaction notes

Loading…