Dimethylformamide → HCID 57665977, compound

HRID 889733Notes

Reaction equation

HRID 889733 reaction equation
[CH2:1]([O:3][C:4](=[O:32])[CH:5]([C:10]1[CH:11]=[C:12]([C:22]2[CH:27]=[CH:26][C:25]([C:28]([F:31])([F:30])[F:29])=[CH:24][CH:23]=2)[CH:13]=[C:14]([CH:16]2[CH2:21][CH2:20][CH2:19][NH:18][CH2:17]2)[CH:15]=1)[CH2:6][CH:7]([CH3:9])[CH3:8])[CH3:2].BrC[C:35]1[CH:44]=[CH:43][C:38]2[N:39]([CH3:42])[N:40]=[N:41][C:37]=2[CH:36]=1.[CH:45](N(C(C)C)CC)(C)C.CN(C=O)C>CC#N.CCOC(C)=O>[CH2:1]([O:3][C:4](=[O:32])[CH:5]([C:10]1[CH:11]=[C:12]([C:22]2[CH:23]=[CH:24][C:25]([C:28]([F:29])([F:30])[F:31])=[CH:26][CH:27]=2)[CH:13]=[C:14]([CH:16]2[CH2:21][CH2:20][CH2:19][N:18]([CH2:45][C:44]3[CH:35]=[CH:36][C:37]4[N:41]=[N:40][N:39]([CH3:42])[C:38]=4[CH:43]=3)[CH2:17]2)[CH:15]=1)[CH2:6][CH:7]([CH3:9])[CH3:8])[CH3:2]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 81531DiisopropylethylamineHCID 27954185-(Bromomethyl)-1-methyl-1H-benzotriazoleHCID 576660204-Methyl-2-(5-piperidin-3-yl-4'-trifluoromethyl-biphenyl-3-yl)-pentanoic acid ethyl ester

Product 1

HCID 57665977HCID 57665977, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of compound 33b, 4-Methyl-2-(5-piperidin-3-yl-4′-trifluoromethyl-biphenyl-3-yl)-pentanoic acid ethyl ester (52.6 mg, 0.118 mmol) in CH3CN (5 ml) was added 5-(Bromomethyl)-1-methyl-1H-1,2,3-benzotriazole (40.0 mg, 0.18 mmol), diisopropylethylamine (41 μl, 0.24 mmol) and DMF)(0.3 ml) to solubolize. The reaction was microwaved at 130° C. for 40 minutes, then at 150° C. for 1 hour 10 min. The reaction was diluted with EtOAc and washed with brine, sat. NaHCO3, and brine, dried and filtered. Purification by silica gel chromatography (Isco) gave the desired product, (67 mg, 96%). Calcd for C33H39F3NO4 (M+H) 592.69, Found 593.4.

Workup

  1. customThe reaction was microwaved at 130° C. for 40 minutes
  2. washwashed with brine, sat. NaHCO3, and brine
  3. customdried
  4. filtrationfiltered
  5. customPurification by silica gel chromatography (Isco)

Sources & evidence

ORD record
ord-eac4ebb069eb48e0b5d20a2c505609d9
Source dataset
uspto-grants-2012_08
Patent number
US08252935B2

Reaction notes

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