Acetyl chloride → HCID 59542961, compound

HRID 1515298Notes

Reaction equation

HRID 1515298 reaction equation
[NH2:1][C@H:2]1[CH2:6][CH2:5][N:4]([CH2:7][CH2:8][C@@H:9]2[CH2:13][S:12][C:11]([C:14]3[NH:15][C:16]4[C:21]([CH:22]=3)=[CH:20][C:19]([Cl:23])=[CH:18][C:17]=4[NH:24][CH:25]3[CH2:30][CH2:29][O:28][CH2:27][CH2:26]3)=[N:10]2)[CH2:3]1.C(N(C(C)C)CC)(C)C.[C:40](Cl)(=[O:42])[CH3:41]>ClCCl>[Cl:23][C:19]1[CH:20]=[C:21]2[C:16](=[C:17]([NH:24][CH:25]3[CH2:30][CH2:29][O:28][CH2:27][CH2:26]3)[CH:18]=1)[NH:15][C:14]([C:11]1[S:12][CH2:13][C@@H:9]([CH2:8][CH2:7][N:4]3[CH2:5][CH2:6][C@H:2]([NH:1][C:40](=[O:42])[CH3:41])[CH2:3]3)[N:10]=1)=[CH:22]2

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 81531DiisopropylethylamineHCID 59543058HCID 59543058, compound

Product 1

HCID 59542961HCID 59542961, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(2-{(R)-4-[2-((S)-3-amino-pyrrolidin-1-yl)-ethyl]-4,5-dihydro-thiazol-2-yl}-5-chloro-1H-indol-7-yl)-(tetrahydro-pyran-4-yl)-amine (85 mg, 0.19 mmol) prepared in Example 170 was dissolved in dichloromethane (10 mL). Diisopropylethylamine (0.13 mL, 0.75 mmol) and acetylchloride (0.013 mL, 0.19 mmol) were added thereto, and the mixture was stirred for 30 min at room temperature. The reaction was quenched by water, and the reaction mixture was extracted with ethyl acetate, dried over anhydrous magnesium sulfate, and filtered. The solvent was removed under reduced pressure, and the residue was purified by column chromatography to give the title compound (39 mg, Yield 42%).

Workup

  1. customThe reaction was quenched by water
  2. extractionthe reaction mixture was extracted with ethyl acetate
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customThe solvent was removed under reduced pressure
  6. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-bcec2635118a491da8d605a1c923722a
Source dataset
uspto-grants-2012_07
Patent number
US08222414B2

Reaction notes

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