Diisopropylethylamine → HCID 178447188, compound

HRID 1428049Notes

Reaction equation

HRID 1428049 reaction equation
FC(F)(F)C(O)=O.[C:8]1([C:14]2[CH:19]=[C:18]([CH:20]3[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]3)[CH:17]=[CH:16][C:15]=2[NH:26][C:27]([C:29]2[NH:30][CH:31]=[C:32]([C:34]#[N:35])[N:33]=2)=[O:28])[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]=1.[C:36]([O:40][C:41]([NH:43][C:44]([CH3:50])([CH3:49])[CH2:45][C:46](O)=[O:47])=[O:42])([CH3:39])([CH3:38])[CH3:37].C1CN([P+](Br)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>ClC(Cl)C.CCOC(C)=O>[C:36]([O:40][C:41](=[O:42])[NH:43][C:44]([CH3:50])([CH3:49])[CH2:45][C:46]([N:23]1[CH2:22][CH2:21][CH:20]([C:18]2[CH:17]=[CH:16][C:15]([NH:26][C:27]([C:29]3[NH:30][CH:31]=[C:32]([C:34]#[N:35])[N:33]=3)=[O:28])=[C:14]([C:8]3[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]=3)[CH:19]=2)[CH2:25][CH2:24]1)=[O:47])([CH3:39])([CH3:37])[CH3:38]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733179PyBroPHCID 103760463-((tert-Butoxycarbonyl)amino)-3-methylbutanoic acidHCID 1785103834-Cyano-1h-imidazole-2-carboxylic acid (2-cyclohex-1-enyl-4-piperidin-4-yl-phenyl)-amide trifluoroacetic acid salt

Product 1

HCID 178447188HCID 178447188, compoundYield 70.2%

Reagents, catalysts & solvents 2

HCID 63651,1-DichloroethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 4-cyano-1H-imidazole-2-carboxylic acid (2-cyclohex-1-enyl-4-piperidin-4-yl-phenyl)-amide trifluoroacetic acid salt (as prepared in Example 14, step (b), 40.0 mg, 0.0818 mmol), 3-tert-butoxycarbonylamino-3-methyl-butyric acid (J. Med. Chem., 34(2), 633-642, (1991), 21.4 mg, 0.0981 mmol) and PyBroP (55.0 mg, 0.0981 mmol) in dichloroethane (2 mL) was added DIEA (43 μL, 0.25 mmol) and the resulting mixture was stirred at RT for 1 day under Ar. The mixture was diluted with EtOAc (30 mL) and washed with H2O (2×10 mL), brine (10 mL), dried over Na2SO4 and then concentrated in vacuo. The residue was purified by flash chomatography (silica gel, 10-40% EtOAc/hexane) to give 33.0 mg (70%) of the title compound as a colorless oil. Mass spectrum (ESI, m/z): Calcd. for C32H42N6O4, 575.3 (M+H). found 574.8.

Workup

  1. washwashed with H2O (2×10 mL), brine (10 mL)
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by flash chomatography (silica gel, 10-40% EtOAc/hexane)

Sources & evidence

ORD record
ord-8b2ce474019b4adaae83936d14fc2d59
Source dataset
uspto-grants-2015_01
Patent number
US08933091B2

Reaction notes

Loading…