Water → HCID 11602205, compound

HRID 916322Notes

Reaction equation

HRID 916322 reaction equation
Cl.[C@H:2]12[CH2:8][C@H:5]([NH:6][CH2:7]1)[CH2:4][N:3]2[C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12]([C:19]#[N:20])=[CH:11][CH:10]=1.C(N(CC)C(C)C)(C)C.[CH3:30][O:31][CH2:32][C:33](Cl)=[O:34].O>ClCCl>[CH3:30][O:31][CH2:32][C:33]([N:6]1[CH2:7][C@@H:2]2[CH2:8][C@H:5]1[CH2:4][N:3]2[C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12]([C:19]#[N:20])=[CH:11][CH:10]=1)=[O:34]

Participants

6

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 96623Methoxyacetyl chlorideHCID 11637791HCID 11637791, compound

Product 1

HCID 11602205HCID 11602205, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

165RL09 (16.5 mg, 0.066 mmol) was dissolved in dichloromethane (1 mL). N,N-Diisopropylethylamine (DIPEA) (9.4 mg, 0.073 mmol) was added followed by methoxyacetyl chloride (7.9 mg, 0.073 mmol). The mixture was shaken in a vial at rt for 18 hours. Water (3 mL) was added and the layers were separated. The aqueous layer was extracted with ethyl acetate (2×5 mL) and the combined organic layers were evaporated. The compound was further purified by column chromatography on silica gel using ethyl acetate/methanol (1:1) to give the title compound (21 mg, 97%).

Workup

  1. customthe layers were separated
  2. extractionThe aqueous layer was extracted with ethyl acetate (2×5 mL)
  3. customthe combined organic layers were evaporated
  4. customThe compound was further purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-d7550359da684c4f870d8a42110f6ac2
Source dataset
uspto-grants-2007_09
Patent number
US07268232B2

Reaction notes

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