Butyryl chloride → N-{3-[2,3-Dimethoxy-6-(1-oxo-indan-4-yl)-phenoxymethyl]-oxetan-3-ylmethyl}-butyramide

HRID 2171039Notes

Reaction equation

HRID 2171039 reaction equation
[NH2:1][CH2:2][C:3]1([CH2:7][O:8][C:9]2[C:14]([O:15][CH3:16])=[C:13]([O:17][CH3:18])[CH:12]=[CH:11][C:10]=2[C:19]2[CH:27]=[CH:26][CH:25]=[C:24]3[C:20]=2[CH2:21][CH2:22][C:23]3=[O:28])[CH2:6][O:5][CH2:4]1.C(N(C(C)C)CC)(C)C.[C:38](Cl)(=[O:42])[CH2:39][CH2:40][CH3:41].COC1C(OC)=CC=C(C2C=CC=C3C=2CCC3=O)C=1OCC1(CNC(=O)C(C)C)COC1>ClCCl.CO>[CH3:16][O:15][C:14]1[C:13]([O:17][CH3:18])=[CH:12][CH:11]=[C:10]([C:19]2[CH:27]=[CH:26][CH:25]=[C:24]3[C:20]=2[CH2:21][CH2:22][C:23]3=[O:28])[C:9]=1[O:8][CH2:7][C:3]1([CH2:2][NH:1][C:38](=[O:42])[CH2:39][CH2:40][CH3:41])[CH2:4][O:5][CH2:6]1

Participants

7

Reactant 4

HCID 8855Butyryl chlorideHCID 81531DiisopropylethylamineHCID 54577377N-{3-[2,3-Dimethoxy-6-(1-oxo-indan-4-yl)-phenoxymethyl]-oxetan-3-ylmethyl}-isobutyramideHCID 674679514-[2-(3-Aminomethyl-oxetan-3-ylmethoxy)-3,4-dimethoxy-phenyl]-indan-1-one2×

Product 1

HCID 67465515N-{3-[2,3-Dimethoxy-6-(1-oxo-indan-4-yl)-phenoxymethyl]-oxetan-3-ylmethyl}-butyramide

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a stirring solution of 4-[2-(3-Aminomethyl-oxetan-3-ylmethoxy)-3,4-dimethoxy-phenyl]-indan-1-one (Compound 191) (150 mg, 0.3916 mmol) in dichloromethane (15 mL), were added diisopropylethylamine (50 mg, 0.390 mmol) and butyryl chloride (41 mg, 0.391 mmol) and the resultant reaction mixture was subjected to the conditions used in the preparation of Compound 193 and purification by column chromatography (silica gel, 0-3% methanol in dichloromethane) afforded the title compound as a solid.

Workup

  1. customthe resultant reaction mixture

Sources & evidence

ORD record
ord-78bcaebe602245449fe3a2ea7d50a69f
Source dataset
uspto-grants-2015_06
Patent number
US09051290B2

Reaction notes

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