Acetic Anhydride → HCID 70896273, compound

HRID 2168479Notes

Reaction equation

HRID 2168479 reaction equation
[OH:1][CH2:2][C:3]1[CH:11]=[CH:10][C:9]2[CH2:12][NH:13][C@@H:14]([CH:17]3[CH:22]4[CH2:23][CH2:24][N:19]([CH2:20][CH2:21]4)[CH2:18]3)[C:15](=[O:16])[N:7]3[C:8]=2[C:4]=1[CH:5]=[CH:6]3.[C:25](OC(=O)C)(=[O:27])[CH3:26]>CN(C)C1C=CN=CC=1.N1C=CC=CC=1>[C:25]([O:1][CH2:2][C:3]1[CH:11]=[CH:10][C:9]2[CH2:12][NH:13][C@@H:14]([CH:17]3[CH:22]4[CH2:21][CH2:20][N:19]([CH2:24][CH2:23]4)[CH2:18]3)[C:15](=[O:16])[N:7]3[C:8]=2[C:4]=1[CH:5]=[CH:6]3)(=[O:27])[CH3:26]

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 70896288HCID 70896288, compound

Product 1

HCID 70896273HCID 70896273, compoundYield 71%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

4-(Dimethylamino)pyridine (13 mg, 0.05 mmol) was added to a solution of (S)-7-(hydroxymethyl)-2-(quinuclidin-3-yl)-3,4-dihydro-[1,4]diazepino[6,7,1-hi]indol-1(2H)-one from Step B above in a mixture of acetic anhydride (0.1 ml, 1.2 mmol) and pyridine (3 ml). The mixture was stirred overnight at room temperature, the solvent was removed under reduced pressure, and the residue was purified by column chromatography (silica gel, 90:10:1 methylene chloride/methanol/concentrated ammonium hydroxide) to afford (S)-(1-oxo-2-(quinuclidin-3-yl)-1,2,3,4-tetrahydro-[1,4]diazepino[6,7,1-hi]indol-7-yl)methyl acetate (124 mg, 71%) as a white solid: MS (ESI+) m/z 368 (M+H).

Workup

  1. customthe solvent was removed under reduced pressure
  2. customthe residue was purified by column chromatography (silica gel, 90:10:1 methylene chloride/methanol/concentrated ammonium hydroxide)

Sources & evidence

ORD record
ord-587dab40279241e39eb0d55f4fbcc688
Source dataset
uspto-grants-2015_06
Patent number
US09045501B2

Reaction notes

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