Triethylorthoaceate → HCID 10045080, compound

HRID 222716

Reaction equation

HRID 222716 reaction equation
[CH2:1](C(CC)(CC)C([O-])([O-])[O-])[CH3:2].[CH:12]1([N:16]2[CH2:22][CH2:21][C:20]3[CH:23]=[CH:24][C:25]([O:27][C:28]4[N:33]=[CH:32][C:31]([C:34]([NH:36][NH2:37])=[O:35])=[CH:30][CH:29]=4)=[CH:26][C:19]=3[CH2:18][CH2:17]2)[CH2:15][CH2:14][CH2:13]1>>[CH:12]1([N:16]2[CH2:22][CH2:21][C:20]3[CH:23]=[CH:24][C:25]([O:27][C:28]4[CH:29]=[CH:30][C:31]([C:34]5[O:35][C:1]([CH3:2])=[N:37][N:36]=5)=[CH:32][N:33]=4)=[CH:26][C:19]=3[CH2:18][CH2:17]2)[CH2:13][CH2:14][CH2:15]1

Participants

3

Reactant 2

HCID 21875354TriethylorthoaceateHCID 57440292HCID 57440292, compound

Product 1

HCID 10045080HCID 10045080, compound

Procedure

A mixture of triethylorthoacetate (3 ml) and 6-[(3-cyclobutyl-2,3,4,5-tetrahydro-1H-3-benzazepin-7-yl)oxy]-3-pyridinecarbohydrazide (D54) (185 mg, 0.52 mmol) was heated at reflux for 16 hours. The reaction mixture was concentrated and the resulting residue was purified by column chromatography eluting with a mixture of 0.880 ammonia:methanol:dichloromethane (0.1:5:95) to afford the title compound (E216). MS (ES+) m/e 377 [M+H]+.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 16 hours
  3. concentrationThe reaction mixture was concentrated
  4. customthe resulting residue was purified by column chromatography
  5. washeluting with a mixture of 0.880 ammonia:methanol:dichloromethane (0.1:5:95)

Sources & evidence

ORD record
ord-ede558de961a4c62a79677478aba2c00
Source dataset
uspto-grants-2012_06
Patent number
US08207331B2

Linked notes

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