Triethylamine → N-(5-((4-(hydroxymethyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl)methyl)-2,3-dihydro-1H-inden-1-yl)-1-methyl-3-(trifluoromethyl)-1H-pyrazole-4-sulfonamide

HRID 43024Notes

Reaction equation

HRID 43024 reaction equation
[NH2:1][CH:2]1[C:10]2[C:5](=[CH:6][C:7]([CH2:11][N:12]3[CH:16]=[C:15]([CH2:17][OH:18])[C:14]([C:19]([F:22])([F:21])[F:20])=[N:13]3)=[CH:8][CH:9]=2)[CH2:4][CH2:3]1.C(N(CC)CC)C.[CH3:30][N:31]1[CH:35]=[C:34]([S:36](Cl)(=[O:38])=[O:37])[C:33]([C:40]([F:43])([F:42])[F:41])=[N:32]1>C(Cl)Cl>[OH:18][CH2:17][C:15]1[C:14]([C:19]([F:22])([F:21])[F:20])=[N:13][N:12]([CH2:11][C:7]2[CH:6]=[C:5]3[C:10](=[CH:9][CH:8]=2)[CH:2]([NH:1][S:36]([C:34]2[C:33]([C:40]([F:43])([F:41])[F:42])=[N:32][N:31]([CH3:30])[CH:35]=2)(=[O:38])=[O:37])[CH2:3][CH2:4]3)[CH:16]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27945611-Methyl-3-(trifluoromethyl)-1H-pyrazole-4-sulfonyl chlorideHCID 58230802(1-((1-Amino-2,3-dihydro-1H-inden-5-yl)methyl)-3-(trifluoromethyl)-1H-pyrazol-4-yl)methanol

Product 1

HCID 53326549N-(5-((4-(hydroxymethyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl)methyl)-2,3-dihydro-1H-inden-1-yl)-1-methyl-3-(trifluoromethyl)-1H-pyrazole-4-sulfonamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (1-((1-amino-2,3-dihydro-1H-inden-5-yl)methyl)-3-(trifluoromethyl)-1H-pyrazol-4-yl)methanol (0.096 mmol, 30 mg) and triethylamine (0.193 mmol, 0.027 mL, 19.50 mg) in DCM (0.9 mL) was added 1-methyl-3-(trifluoromethyl)-1H-pyrazole-4-sulfonyl chloride (0.096 mmol, 23.96 mg) and the whole stirred at room temperature overnight. The reaction mixture was concentrated under reduced pressure and the residue purified by RP-HPLC to give a clear film (12.0 mg, 0.023 mmol, 23.8%). MS (ESI): m/z [M+H]+ 524.0.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue purified by RP-HPLC
  3. customto give a clear film (12.0 mg, 0.023 mmol, 23.8%)

Sources & evidence

ORD record
ord-f77c6ad3e18f4285bce73753e2dec1e1
Source dataset
uspto-grants-2013_09
Patent number
US08536214B2

Reaction notes

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