Acetic Anhydride → HCID 86761758, compound

HRID 1809114Notes

Reaction equation

HRID 1809114 reaction equation
[N:1]1([C:11]([C:13]2[CH:17]=[C:16]([CH:18]3[CH2:22][CH2:21][NH:20][CH2:19]3)[S:15][CH:14]=2)=[O:12])[C@@H:10]2[C@@H:5]([CH2:6][CH2:7][CH2:8][CH2:9]2)[CH2:4][CH2:3][CH2:2]1.[C:23](OC(=O)C)(=[O:25])[CH3:24]>C(N(CC)CC)C>[N:1]1([C:11]([C:13]2[CH:17]=[C:16]([CH:18]3[CH2:22][CH2:21][N:20]([C:23](=[O:25])[CH3:24])[CH2:19]3)[S:15][CH:14]=2)=[O:12])[C@@H:10]2[C@@H:5]([CH2:6][CH2:7][CH2:8][CH2:9]2)[CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 86761759HCID 86761759, compound

Product 1

HCID 86761758HCID 86761758, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

cis-(Octahydro-quinolin-1-yl)-(5-pyrrolidin-3-yl-thiophen-3-yl)-methanone (CC-177) (0.065 g, 0.19 mmol) was dissolved in triethylamine (2 mL) and acetic anhydride was added and the resulting mixture stirred for 20 minutes. The solvent was evaporated and the resulting gum was purified by HPLC eluting with 10%-98% acetonitrile in water (0.1% formic acid). The fractions containing the desired product were concentrated under vacuum to give the title compound (0.029 g). LCMS m/z 361.20[M+H]+ RT=9.24 min (Analytical Method 2).

Workup

  1. customThe solvent was evaporated
  2. customthe resulting gum was purified by HPLC
  3. washeluting with 10%-98% acetonitrile in water (0.1% formic acid)
  4. additionThe fractions containing the desired product
  5. concentrationwere concentrated under vacuum

Sources & evidence

ORD record
ord-7270b247b2f345f48d46640339067ca1
Source dataset
uspto-grants-2013_01
Patent number
US08362008B2

Reaction notes

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