Triethylamine → HCID 66796138, compound

HRID 2043773Notes

Reaction equation

HRID 2043773 reaction equation
[CH3:1][NH:2][C@H:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH2:6][CH2:5][C@@H:4]1[CH3:13].C(N(CC)CC)C.[CH3:21][C:22]1[N:26]([CH2:27][C:28]([N:30]2[CH2:35][CH2:34][CH:33]([C:36]3[S:37][CH:38]=[C:39]([C:41](Cl)=[O:42])[N:40]=3)[CH2:32][CH2:31]2)=[O:29])[N:25]=[C:24]([C:44]([F:47])([F:46])[F:45])[CH:23]=1>ClCCl>[CH3:1][N:2]([C@H:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH2:6][CH2:5][C@@H:4]1[CH3:13])[C:41]([C:39]1[N:40]=[C:36]([CH:33]2[CH2:34][CH2:35][N:30]([C:28](=[O:29])[CH2:27][N:26]3[C:22]([CH3:21])=[CH:23][C:24]([C:44]([F:45])([F:47])[F:46])=[N:25]3)[CH2:31][CH2:32]2)[S:37][CH:38]=1)=[O:42]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 67460199HCID 67460199, compoundHCID 866377272-[1-[[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl]-4-piperidinyl]-4-thiazolecarbonyl chloride2×

Product 1

HCID 66796138HCID 66796138, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of (1R,2S)-1,2,3,4-tetrahydro-N,2-dimethyl-naphthalenamine and its enantiomer (0.043 g, 0.25 mmol) (prepared by the method described from Example 6, Step A) and triethylamine (0.104 mL, 0.74 mmol) in 2 mL of dichloromethane was gradually added 2-[1-[[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl]-4-piperidinyl]-4-thiazolecarbonyl chloride (85 mg, 0.2 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 sodium sulfate and concentrated in vacuo. The crude product was purified by medium-pressure liquid chromatography on silica gel using 60-100% of ethyl acetate in hexanes as eluant to give 43 mg of the title compounds, compounds of the present invention as 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 sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by medium-pressure liquid chromatography on silica gel using 60-100% of ethyl acetate in hexanes as eluant

Sources & evidence

ORD record
ord-7ec99abdd12f4a6dbc6879e41c22ce77
Source dataset
uspto-grants-2013_11
Patent number
US08586611B2

Reaction notes

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