Acetyl chloride → HCID 69489389, compound

HRID 1350488Notes

Reaction equation

HRID 1350488 reaction equation
C([Cl:4])(=O)C.[F:5][C:6]1[CH:7]=[CH:8][C:9]2[N:18]=[C:17]([N:19]3[CH2:24][CH2:23][N:22]([CH3:25])[C@@H:21]([CH2:26][CH2:27][C:28]4[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[CH:30][CH:29]=4)[CH2:20]3)[C:16]3[C:15]4[CH:36]=[CH:37][CH:38]=[CH:39][C:14]=4[S:13][C:12]=3[NH:11][C:10]=2[CH:40]=1>C(O)C.C(#N)C.O>[ClH:4].[ClH:4].[F:5][C:6]1[CH:7]=[CH:8][C:9]2[N:18]=[C:17]([N:19]3[CH2:24][CH2:23][N:22]([CH3:25])[C@@H:21]([CH2:26][CH2:27][C:28]4[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[CH:30][CH:29]=4)[CH2:20]3)[C:16]3[C:15]4[CH:36]=[CH:37][CH:38]=[CH:39][C:14]=4[S:13][C:12]=3[NH:11][C:10]=2[CH:40]=1

Participants

5

Reactant 2

HCID 6367Acetyl chlorideHCID 58860668HCID 58860668, compound

Product 1

HCID 69489389HCID 69489389, compoundYield 104.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 18373917Acetonitrile--water (1/1)Solvent

Procedure

Add a solution of acetyl chloride (0.144 mL, 2.02 mmol) in absolute ethanol to a solution of (S)-9-fluoro-5-{3-[2-(4-methoxy-phenyl)-ethyl]-4-methyl-piperazin-1-yl}-11H-12-thia-6,11-diaza-dibenzo[a,f]azulene (0.174 g, 0.348 mmol) in absolute ethanol and stir briefly at ambient temperature. Concentrate solution under reduced pressure to give an orange solid. Reconstitute the solid in acetonitrile: water (1:1), freeze-dry the solution in a dry-ice/acetone bath, and lyophilize overnight to give the title compound (0.208 g) as a yellow solid: mass spectrum (APCI+, m/e): 501 (M+1–2HCl); exact mass spectrum (ES+, m/e, C29H29FN4OS.2HCl): calc. 501.2124 (M+1–2HCl), found 501.2130.

Workup

  1. customConcentrate solution under reduced pressure to give an orange solid
  2. customfreeze-dry the solution in a dry-ice/acetone bath

Sources & evidence

ORD record
ord-c12249f49b9f4f9589fee4048ce12638
Source dataset
uspto-grants-2007_05
Patent number
US07214673B2

Reaction notes

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