Isobutyric Acid → N-(5-((4-(Hydroxymethyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl)methyl)-2,3-dihydro-1H-inden-1-yl)isobutyramide

HRID 43027Notes

Reaction equation

HRID 43027 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:23](O)(=[O:27])[CH:24]([CH3:26])[CH3:25].C(N(CC)CC)C.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.CCN=C=NCCCN(C)C>CN(C=O)C>[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][C:23](=[O:27])[CH:24]([CH3:26])[CH3:25])[CH2:3][CH2:4]3)[CH:16]=1

Participants

7

Reactant 5

HCID 6590Isobutyric AcidHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 25127565Edci wscHCID 58230802(1-((1-Amino-2,3-dihydro-1H-inden-5-yl)methyl)-3-(trifluoromethyl)-1H-pyrazol-4-yl)methanol

Product 1

HCID 67088099N-(5-((4-(Hydroxymethyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl)methyl)-2,3-dihydro-1H-inden-1-yl)isobutyramideYield 29.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

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), isobutyric acid (0.096 mmol, 8.94 μL 8.49 mg), triethylamine (0.193 mmol, 0.027 ml, 19.50 mg) and HOBt (0.096 mmol, 13.02 mg) in DMF (0.8 mL) was added EDCI/WSC (0.096 mmol, 18.47 mg). The whole was stirred at room temperature overnight before the reaction mixture was quenched by the addition of MeOH (100 μL) before being purified by prep HPLC to give a white solid (10.8 mg, 0.028 mmol, 29.4%). MS (ESI): m/z [M+H]+ 382.2

Workup

  1. customwas quenched by the addition of MeOH (100 μL)
  2. custombefore being purified by prep HPLC

Sources & evidence

ORD record
ord-e4d6e30b3c9e4b2e8de4bb32c437376d
Source dataset
uspto-grants-2013_09
Patent number
US08536214B2

Reaction notes

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