Dimethylformamide dimethyl acetal → HCID 67491285, compound

HRID 571968Notes

Reaction equation

HRID 571968 reaction equation
CO[CH:3](OC)[N:4]([CH3:6])[CH3:5].[C:9]([C:12]1[CH:13]=[C:14]([S:22]([NH:25][C@H:26]2[CH2:31][CH2:30][CH2:29][C@@H:28]([N:32]3[CH:36]=[N:35][N:34]=[CH:33]3)[CH2:27]2)(=[O:24])=[O:23])[CH:15]=[C:16]([C:18]([F:21])([F:20])[F:19])[CH:17]=1)(=[O:11])[CH3:10]>CCO>[CH3:6][N:4]([CH3:5])/[CH:3]=[CH:10]/[C:9]([C:12]1[CH:13]=[C:14]([S:22]([NH:25][C@H:26]2[CH2:31][CH2:30][CH2:29][C@@H:28]([N:32]3[CH:33]=[N:34][N:35]=[CH:36]3)[CH2:27]2)(=[O:23])=[O:24])[CH:15]=[C:16]([C:18]([F:20])([F:19])[F:21])[CH:17]=1)=[O:11]

Participants

4

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 67491110HCID 67491110, compound

Product 1

HCID 67491285HCID 67491285, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
100 °C

Procedure

N,N,-Dimethylformamide dimethyl acetal (200 μL, 1.49 mmol) was added to a stirred solution of 9a (100 mg, 0.240 mmol) in EtOH (1.50 mL). The mixture was placed in a sealed tube and heated in a microwave reactor at 100° C. for 2 h. After cooling to rt, the reaction mixture was concentrated in vacuo, and the resulting crude residue was purified by preparative thin layer chromatography on silica gel (10% MeOH/DCM as eluent) to afford the title compound, 9b. m/z (ES) 472 (MH)+

Workup

  1. customThe mixture was placed in a sealed tube
  2. temperatureAfter cooling to rt
  3. concentrationthe reaction mixture was concentrated in vacuo
  4. customthe resulting crude residue was purified by preparative thin layer chromatography on silica gel (10% MeOH/DCM as eluent)

Sources & evidence

ORD record
ord-64bceb86ed774c48a7d8ac11575e903c
Source dataset
uspto-grants-2015_05
Patent number
US09029377B2

Reaction notes

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