Acetyl chloride → HCID 22250079, compound

HRID 889889Notes

Reaction equation

HRID 889889 reaction equation
[CH3:1][O:2][CH2:3][C@H:4]1[CH2:8][CH2:7][CH2:6][N:5]1[C:9]([C:11]1[S:19][C:18]2[C:13](=[N:14][CH:15]=[CH:16][C:17]=2[O:20][C:21]2[CH:22]=[C:23]3[C:27](=[CH:28][CH:29]=2)[NH:26][C:25]([CH3:30])=[CH:24]3)[CH:12]=1)=[O:10].[C:31](Cl)(=[O:33])[CH3:32]>CN(C1C=CN=CC=1)C.CN(C=O)C>[CH3:1][O:2][CH2:3][CH:4]1[CH2:8][CH2:7][CH2:6][N:5]1[C:9]([C:11]1[S:19][C:18]2[C:13](=[N:14][CH:15]=[CH:16][C:17]=2[O:20][C:21]2[CH:22]=[C:23]3[C:27](=[CH:28][CH:29]=2)[N:26]([C:31](=[O:33])[CH3:32])[C:25]([CH3:30])=[CH:24]3)[CH:12]=1)=[O:10]

Participants

5

Reactant 2

HCID 6367Acetyl chlorideHCID 10159192HCID 10159192, compound

Product 1

HCID 22250079HCID 22250079, compoundYield 69%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

To a solution of (2R)-(2-methoxymethyl-pyrrolidin-1-yl)-[7-(2-methyl-1H-indol-5-yloxy)-thieno[3,2-b]pyridin-2-yl]-methanone and DMAP (120 mg, 0.28 mmol) in DMF (5 mL) was added acetyl chloride (44 mg, 0.56 mmol). After 3 h the reaction was quenched with water (5 mL). The aqueous layer was extracted with CH2Cl2 (2×15 mL). The combined organic extracts were dried (Na2SO4), and concentrated onto silica gel (5 mL). Purification by flash chromatography on silica gel (CH2Cl2/MeOH 97:3) afforded the title compound as a white solid (0.36 g, 69%). MS: 464 (MH+); HPLC Rf: 6.12 min; HPLC purity: 96%.

Workup

  1. customAfter 3 h the reaction was quenched with water (5 mL)
  2. extractionThe aqueous layer was extracted with CH2Cl2 (2×15 mL)
  3. dry with materialThe combined organic extracts were dried (Na2SO4)
  4. concentrationconcentrated onto silica gel (5 mL)
  5. customPurification by flash chromatography on silica gel (CH2Cl2/MeOH 97:3)

Sources & evidence

ORD record
ord-8fb02104e85e4a73823bd3a7ed1648bb
Source dataset
uspto-grants-2006_02
Patent number
US06995171B2

Reaction notes

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