Triethylamine → N-(2,3-dihydro-2-methyl-1H-inden-1-yl)-N-methyl-2-[1-[[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl]-4-piperidinyl]-4-thiazolecarboxamide

HRID 2043769Notes

Reaction equation

HRID 2043769 reaction equation
[CH3:1][NH:2][CH:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5][CH:4]1[CH3:12].C(N(CC)CC)C.[CH3:20][C:21]1[N:25]([CH2:26][C:27]([N:29]2[CH2:34][CH2:33][CH:32]([C:35]3[S:36][CH:37]=[C:38]([C:40](Cl)=[O:41])[N:39]=3)[CH2:31][CH2:30]2)=[O:28])[N:24]=[C:23]([C:43]([F:46])([F:45])[F:44])[CH:22]=1>ClCCl>[CH3:12][CH:4]1[CH2:5][C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[CH:3]1[N:2]([CH3:1])[C:40]([C:38]1[N:39]=[C:35]([CH:32]2[CH2:31][CH2:30][N:29]([C:27](=[O:28])[CH2:26][N:25]3[C:21]([CH3:20])=[CH:22][C:23]([C:43]([F:44])([F:45])[F:46])=[N:24]3)[CH2:34][CH2:33]2)[S:36][CH:37]=1)=[O:41]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 617511972,3-dihydro-N,2-dimethyl-1H-inden-1-amineHCID 866377272-[1-[[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl]-4-piperidinyl]-4-thiazolecarbonyl chloride2×

Product 1

HCID 66795913N-(2,3-dihydro-2-methyl-1H-inden-1-yl)-N-methyl-2-[1-[[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl]-4-piperidinyl]-4-thiazolecarboxamideYield 39.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 2,3-dihydro-N,2-dimethyl-1H-inden-1-amine (177 mg, 1.1 mmol) and triethylamine (0.22 mL, 1.6 mmol) in 5 mL of dichloromethane was gradually added 2-[1-[[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl]-4-piperidinyl]-4-thiazolecarbonyl chloride (421 mg, 1 mmol) (i.e. the product of Example 19, Step D) at 0° C. The reaction mixture was stirred at room temperature for 16 h, diluted with 4 mL of dichloromethane, and washed with water, 1 N aqueous hydrochloric acid, water, saturated solution of sodium bicarbonate and brine. The filtered reaction mixture was dried over magnesium sulfate and concentrated in vacuo to give 215 mg of the title compound, the product of present invention as a white foam.

Workup

  1. customat 0° C
  2. washwashed with water, 1 N aqueous hydrochloric acid, water, saturated solution of sodium bicarbonate and brine
  3. customThe filtered reaction mixture
  4. dry with materialwas dried over magnesium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-32a8ddc848924e2c974cde9b2bb7f505
Source dataset
uspto-grants-2013_11
Patent number
US08586611B2

Reaction notes

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