Methanol → HCID 178424457, compound

HRID 1992038Notes

Reaction equation

HRID 1992038 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[CH:19]=[CH:18][C:17]([NH:20][C:21]([C:23]3[N:24](COCC[Si](C)(C)C)[CH:25]=[C:26]([C:28]#[N:29])[N:27]=3)=[O:22])=[C:16]([C:38]3[CH2:43][CH2:42][C:41]([CH3:45])([CH3:44])[CH2:40][CH:39]=3)[CH:15]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.CO.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:44][C:41]1([CH3:45])[CH2:42][CH2:43][C:38]([C:16]2[CH:15]=[C:14]([CH:11]3[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]3)[CH:19]=[CH:18][C:17]=2[NH:20][C:21]([C:23]2[NH:24][CH:25]=[C:26]([C:28]#[N:29])[N:27]=2)=[O:22])=[CH:39][CH2:40]1

Participants

5

Reactant 3

HCID 887MethanolHCID 6422Trifluoroacetic acidHCID 58694585HCID 58694585, compound

Product 1

HCID 178424457HCID 178424457, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 124 mg (0.196 mmol) 4-[4-{[4-cyano-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole-2-carbonyl]-amino}-3-(4,4-dimethyl-cyclohex-1-enyl)-phenyl]-piperidine-1-carboxylic acid tert-butyl ester (as prepared in the previous step) in 10 mL CH2Cl2 was treated with 200 μL MeOH and 3 mL TFA at RT for 3.5 h. Solvents were evaporated in vacuo. The residue was taken up in CH2Cl2 (30 mL) and washed with saturated aqueous NaHCO3 (1×20 mL). The organic layer was dried (MgSO4) and concentrated in vacuo to afford 70.0 mg (89%) of the title compound as a white solid: Mass spectrum (ESI, m/z): Calcd. for C24H29N5O, 404.2 (M+H), found 404.3.

Workup

  1. customSolvents were evaporated in vacuo
  2. washwashed with saturated aqueous NaHCO3 (1×20 mL)
  3. dry with materialThe organic layer was dried (MgSO4)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-047ce6dcc9d743c9b4c69e64428884ec
Source dataset
uspto-grants-2010_01
Patent number
US07645755B2

Reaction notes

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