Dimethylformamide dimethyl acetal → HCID 21905771, compound

HRID 348020Notes

Reaction equation

HRID 348020 reaction equation
[CH3:1]OC(OC)N(C)C.[CH:9]([N:22]1[CH2:25][C:24]([NH:29][CH3:30])([C:26]([NH2:28])=[O:27])[CH2:23]1)([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>>[CH:9]([N:22]1[CH2:25][C:24]2([C:26](=[O:27])[N:28]=[CH:30][N:29]2[CH3:1])[CH2:23]1)([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

3

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 58721711HCID 58721711, compound

Product 1

HCID 21905771HCID 21905771, compoundYield 96%

Procedure

N,N-Dimethylformamide dimethyl acetal (1.1 ml, 8.3 mmol) was combined with 1-benzhydryl-3-methylaminoazetidine-3-carboxylic acid amide (I-3A-2b; 153 mg, 0.52 mmol) and heated to reflux. After 3 hours, the suspension was cooled and extracted from saturated aqueous NaHCO3 with ethyl acetate. The combined extracts were dried (Na2SO4) and concentrated, in vacuo, to afford I-5A-10a as a solid (152 mg, 96%): +ESI MS (M+1) 306.3; 1H NMR (400 MHz, CD3OD) δ 8.42 (s, 1H), 7.47 (d, J=7.5 Hz, 4H), 7.27 (t, J=7.5 Hz, 4H), 7.17 (t, J=7.5 Hz, 2H), 4.57 (s, 1H), 3.58 (s, 3H), 3.55 (d, J=10.0 Hz, 2H), 3.34 (d, J=10.0 Hz, 2H).

Workup

  1. temperatureheated to reflux
  2. temperaturethe suspension was cooled
  3. extractionextracted from saturated aqueous NaHCO3 with ethyl acetate
  4. dry with materialThe combined extracts were dried (Na2SO4)
  5. concentrationconcentrated, in vacuo

Sources & evidence

ORD record
ord-748701157d8a41c08b49f42a0e4e4d4e
Source dataset
uspto-grants-2007_02
Patent number
US07176210B2

Reaction notes

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