Dimethylformamide → HCID 71075185, compound

HRID 1852033Notes

Reaction equation

HRID 1852033 reaction equation
[NH:1]([C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:11]1[CH:16]=[CH:15][C:14]([CH2:17][N:18]2[C:26]3[C:21](=[CH:22][C:23]([C:27]([NH:29][C@H:30]([C:32]4[CH:37]=[CH:36][CH:35]=[C:34]([CH:38]([CH3:40])[CH3:39])[CH:33]=4)[CH3:31])=[O:28])=[CH:24][CH:25]=3)[C:20]([CH3:41])=[C:19]2[CH3:42])=[CH:13][CH:12]=1)=[O:4])[NH2:2].CCN(C(C)C)C(C)C.CN([CH:55]=[O:56])C>>[CH:38]([C:34]1[CH:33]=[C:32]([C@@H:30]([NH:29][C:27]([C:23]2[CH:22]=[C:21]3[C:26](=[CH:25][CH:24]=2)[N:18]([CH2:17][C:14]2[CH:13]=[CH:12][C:11]([C:6]4[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=4[C:3]4[O:4][C:55](=[O:56])[NH:2][N:1]=4)=[CH:16][CH:15]=2)[C:19]([CH3:42])=[C:20]3[CH3:41])=[O:28])[CH3:31])[CH:37]=[CH:36][CH:35]=1)([CH3:39])[CH3:40]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 81531DiisopropylethylamineHCID 71074680HCID 71074680, compound

Product 1

HCID 71075185HCID 71075185, compound

Procedure

The mixture of (S)-1-((2′-(hydrazinocarbonyl)-[1,1′-biphenyl]-4-yl)methyl)-N-(1-(3-isopropylphenyl)ethyl)-2,3-dimethyl-1H-indole-5-carboxamide (0.062 g, 0.11 mmol), N,N′-carbonyldiimidazole (0.027 g, 0.16 mmol) and DIEA (0.03 mL, 0.16 mmol) in DMF was stirred at room temperature for 1 h, and then stirred at 50° C. for 1 h. The reaction mixture was poured on to ice-water, and then extracted with ethyl acetate. The combined organic layers were washed with water and brine. The solvent was remove and the residue was purified with preparative-HPLC to obtain the title compound. ESI-MS (m/z): 585 [M+H]+.

Workup

  1. stirringstirred at 50° C. for 1 h
  2. extractionextracted with ethyl acetate
  3. washThe combined organic layers were washed with water and brine
  4. customThe solvent was remove
  5. customthe residue was purified with preparative-HPLC

Sources & evidence

ORD record
ord-84ccacb90ba14dff8c6d9aa4e1355f72
Source dataset
uspto-grants-2015_02
Patent number
US08957093B2

Reaction notes

Loading…