Hydrochloric Acid → HCID 66795948, compound

HRID 2043768Notes

Reaction equation

HRID 2043768 reaction equation
[CH3:1][C:2]1[N:6]([CH2:7][C:8]([N:10]2[CH2:15][CH2:14][CH:13]([C:16]3[S:17][CH:18]=[C:19]([C:21](Cl)=[O:22])[N:20]=3)[CH2:12][CH2:11]2)=[O:9])[N:5]=[C:4]([C:24]([F:27])([F:26])[F:25])[CH:3]=1.[CH3:28][NH:29][C@H:30]1[C:38]2[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=2)[CH2:32][CH:31]1C.C(N(CC)CC)C.Cl>ClCCl>[C@H:30]1([N:29]([CH3:28])[C:21]([C:19]2[N:20]=[C:16]([CH:13]3[CH2:14][CH2:15][N:10]([C:8](=[O:9])[CH2:7][N:6]4[C:2]([CH3:1])=[CH:3][C:4]([C:24]([F:27])([F:26])[F:25])=[N:5]4)[CH2:11][CH2:12]3)[S:17][CH:18]=2)=[O:22])[C:38]2[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=2)[CH2:32][CH2:31]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 67460057HCID 67460057, compoundHCID 866377272-[1-[[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl]-4-piperidinyl]-4-thiazolecarbonyl chloride2×

Product 1

HCID 66795948HCID 66795948, compoundYield 80.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-[1-[[5-Methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl]-4-piperidinyl]-4-thiazolecarbonyl chloride (210 mg, 0.5 mmol) (i.e. the product of Example 19, Step D) was treated with a solution of (1R)-2,3-dihydro-N,2-dimethyl-1H-inden-1-amine (147 μL, 1.0 mmol) and triethylamine (139 μL, 1.0 mmol) in 5 mL of dichloromethane. The reaction mixture was stirred at room temperature for 2 h, passed through a Varian 1005 Chem Elut™ column pretreated with 3 mL of 1 N aqueous hydrochloric acid. The column was flushed with three column volumes of dichloromethane. The collected dichloromethane solution was evaporated in vacuo and purified by medium-pressure liquid chromatography on silica gel using 50-100% of ethyl acetate in 1-chlorobutane as eluant to give 214 mg of the title compound, the product of present invention as a white foam.

Workup

  1. customThe column was flushed with three column volumes of dichloromethane
  2. customThe collected dichloromethane solution was evaporated in vacuo
  3. custompurified by medium-pressure liquid chromatography on silica gel using 50-100% of ethyl acetate in 1-chlorobutane as eluant

Sources & evidence

ORD record
ord-f3131614f15d4ba79f1d173981d0e7ce
Source dataset
uspto-grants-2013_11
Patent number
US08586611B2

Reaction notes

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