Ethanol → HCID 178457461, compound

HRID 1991993Notes

Reaction equation

HRID 1991993 reaction equation
C(OC(=O)[NH:7][C:8]([CH3:41])([CH3:40])[CH2:9][C:10]([N:12]1[CH2:17][CH2:16][CH:15]([C:18]2[CH:23]=[CH:22][C:21]([NH:24][C:25]([C:27]3[NH:28][CH:29]=[C:30]([C:32]#[N:33])[N:31]=3)=[O:26])=[C:20]([C:34]3[CH2:39][CH2:38][CH2:37][CH2:36][CH:35]=3)[CH:19]=2)[CH2:14][CH2:13]1)=[O:11])(C)(C)C.CCO.[C:46]([OH:52])([C:48]([F:51])([F:50])[F:49])=[O:47]>C(Cl)Cl.C(O)CC>[F:49][C:48]([F:51])([F:50])[C:46]([OH:52])=[O:47].[NH2:7][C:8]([CH3:41])([CH3:40])[CH2:9][C:10]([N:12]1[CH2:17][CH2:16][CH:15]([C:18]2[CH:23]=[CH:22][C:21]([NH:24][C:25]([C:27]3[NH:28][CH:29]=[C:30]([C:32]#[N:33])[N:31]=3)=[O:26])=[C:20]([C:34]3[CH2:39][CH2:38][CH2:37][CH2:36][CH:35]=3)[CH:19]=2)[CH2:14][CH2:13]1)=[O:11]

Participants

6

Reactant 3

HCID 702EthanolHCID 6422Trifluoroacetic acidHCID 178447188HCID 178447188, compound

Product 1

HCID 178457461HCID 178457461, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 10311-PropanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of [3-(4-{4-[(4-cyano-1H-imidazole-2-carbonyl)-amino]-3-cyclohex-1-enyl-phenyl}-piperidin-1-yl)-1,1-dimethyl-3-oxo-propyl]-carbamic acid tert-butyl ester (33.0 mg, 0.0574 mmol) (as prepared in the previous step) in 3 mL of DCM and 0.10 mL EtOH at 0° C. was added 1.0 mL of TFA, the mixture was warmed to RT and stirred for 3 h. The reaction was diluted with 3 mL of n-PrOH and then concentrated in vacuo. The residue was purified by flash chomatography (silica gel, 3-8% MeOH/DCM) to give 33.5 mg (99%) of the title compound as a white solid. 1H-NMR (400 MHz, CDCl3): δ 13.3 (s, 1H), 9.52 (s, 1H), 8.57 (br s, 3H), 8.26 (d, 1H, J=8.6 Hz), 7.69 (s, 1H), 7.02 (dd, 1H, J=8.6, 1.7 Hz), 6.98 (d, 1H, J=1.7 Hz), 5.78 (m, 1H), 4.67 (br d, 1H, J=13.4 Hz), 3.88 (br d, 1H, J=13.4 Hz), 3.10 (m, 1H), 2.55-2.85 (m, 4H), 2.23 (m, 4H), 1.72-2.01 (m, 8H), 1.50 (s, 6H). Mass spectrum (ESI, m/z): Calcd. for C27H34N6O2, 475.3 (M+H), found 475.1.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was purified by flash chomatography (silica gel, 3-8% MeOH/DCM)

Sources & evidence

ORD record
ord-8227085c2cae4b5fac1acb6b0295db56
Source dataset
uspto-grants-2010_01
Patent number
US07645755B2

Reaction notes

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