Acetyl chloride → HCID 86728309, compound

HRID 1776931Notes

Reaction equation

HRID 1776931 reaction equation
[F:1][C:2]1[C:3]2[CH:4]=[C:5]3[C:14]4[N:15]=[C:16]([C:19]5[C:20]([N:39]([CH3:44])[S:40]([CH3:43])(=[O:42])=[O:41])=[CH:21][C:22]6[O:26][C:25]([C:27]7[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=7)=[C:24]([C:34]([NH:36][CH3:37])=[O:35])[C:23]=6[CH:38]=5)[CH:17]=[CH:18][C:13]=4[O:12][CH2:11][N:6]3[C:7]=2[CH:8]=[CH:9][CH:10]=1.[C:45](Cl)(=[O:47])[CH3:46].COC(O[Si](C)(C)C)=C(C)C>ClCCl>[C:45]([N:36]([CH3:37])[C:34]([C:24]1[C:23]2[CH:38]=[C:19]([C:16]3[CH:17]=[CH:18][C:13]4[O:12][CH2:11][N:6]5[C:7]6[CH:8]=[CH:9][CH:10]=[C:2]([F:1])[C:3]=6[CH:4]=[C:5]5[C:14]=4[N:15]=3)[C:20]([N:39]([CH3:44])[S:40]([CH3:43])(=[O:42])=[O:41])=[CH:21][C:22]=2[O:26][C:25]=1[C:27]1[CH:28]=[CH:29][C:30]([F:33])=[CH:31][CH:32]=1)=[O:35])(=[O:47])[CH3:46]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 552336Silane, ((1-methoxy-2-methyl-1-propenyl)oxy)trimethyl-HCID 715091141426960-33-9

Product 1

HCID 86728309HCID 86728309, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-(11-fluoro-6H-pyrido[2′,3′:5,6][1,3]oxazino[3,4-a]indol-2-yl)-2-(4-fluorophenyl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide (500 mg, 0.81 mmol) in dichloromethane (2 ml) was added acetyl chloride (174 μl, 2.44 mmol) and ((1-methoxy-2-methylprop-1-en-1-yl)oxy)trimethylsilane (495 μl, 2.44 mmol). The resulting mixture was stirred at room temperature overnight. Concentrated in vacuo and added Et3N (5 ml). Silica gel chromatography (eluted with 0-5% MeOH/dichloromethane) to provide N-acetyl-5-(11-fluoro-6H-pyrido[2′,3′:5,6][1,3]oxazino[3,4-a]indol-2-yl)-2-(4-fluorophenyl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide (500 mg, yield: 94%) MS (M+H)+: 657.

Workup

  1. concentrationConcentrated in vacuo
  2. additionadded Et3N (5 ml)
  3. washSilica gel chromatography (eluted with 0-5% MeOH/dichloromethane)

Sources & evidence

ORD record
ord-1adb1b4576f444968ad8c879eca7dd7f
Source dataset
uspto-grants-2016_02
Patent number
US09265773B2

Reaction notes

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