Diisopropylethylamine → HCID 57665987, compound

HRID 889731Notes

Reaction equation

HRID 889731 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:36]=[CH:37][C:38]2[S:42][N:41]=[N:40][C:39]=2[CH:43]=1.[CH:44](N(C(C)C)CC)(C)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]([CH2:44][C:36]3[CH:35]=[CH:43][C:39]4[N:40]=[N:41][S:42][C:38]=4[CH:37]=3)[CH2:17]2)[CH:15]=1)[CH2:6][CH:7]([CH3:9])[CH3:8])[CH3:2]

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 27952105-(bromomethyl)-1,2,3-benzothiadiazoleHCID 576660204-Methyl-2-(5-piperidin-3-yl-4'-trifluoromethyl-biphenyl-3-yl)-pentanoic acid ethyl ester

Product 1

HCID 57665987HCID 57665987, compoundYield 89%

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 (59.3 mg, 0.133 mmol) in CH3CN (5 ml) was added 5Bromomethyl-benzo 1,2,3 thiadiazole (45.5 mg, 0.20 mmol) and diisopropylethylamine (46 μl, 0.27 mmol). The reaction was microwaved at 130° C. for 10 minutes, then diluted with EtOAc and washed with brine, sat. NaHCO3, and brine, dried and filtered. Purification by silica gel chromatography (Isco) gave the desired product, (70 mg, 89%). Calcd for C33H36F3N3O2S (M+H) 595.72, Found 597.3.

Workup

  1. customThe reaction was microwaved at 130° C. for 10 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-7c405295571842c2825a820d9e1562ed
Source dataset
uspto-grants-2012_08
Patent number
US08252935B2

Reaction notes

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