Acetic Anhydride → HCID 57656851, compound

HRID 2371178Notes

Reaction equation

HRID 2371178 reaction equation
C(N(CC)CC)C.[NH:8]1[CH2:11][CH:10]([N:12]2[CH2:17][CH2:16][O:15][C@@H:14]([CH2:18][N:19]3[CH2:24][CH2:23][N:22]([C:25]([NH:27][C:28]4[CH:33]=[CH:32][C:31]([Cl:34])=[C:30]([Cl:35])[CH:29]=4)=[O:26])[CH2:21][CH2:20]3)[CH2:13]2)[CH2:9]1.[CH3:36][C:37](OC(C)=O)=[O:38]>C(Cl)Cl>[C:37]([N:8]1[CH2:9][CH:10]([N:12]2[CH2:17][CH2:16][O:15][C@@H:14]([CH2:18][N:19]3[CH2:20][CH2:21][N:22]([C:25]([NH:27][C:28]4[CH:33]=[CH:32][C:31]([Cl:34])=[C:30]([Cl:35])[CH:29]=4)=[O:26])[CH2:23][CH2:24]3)[CH2:13]2)[CH2:11]1)(=[O:38])[CH3:36]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 67220788HCID 67220788, compound

Product 1

HCID 57656851HCID 57656851, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triethylamine (61 uL) was added to a stirring solution of 4-{[(25)-4-azetidin-3-ylmorpholin-2-yl]methyl}-N-(3,4-dichlorophenyl)piperazine-1-carboxamide (125 mg) in DCM (5 ml) followed by Ac2O (30 uL) and the reaction was stirred for 3 h. The reaction was then quenched by addition of 1M NaOH (aq.) (10 ml) and DCM (15 ml). The organic layer was separated and dried (MgSO4), filtered and evaporated. Purification by column chromatography 5-10% MeOH:DCM afforded the title compound (31 mg) as a white foam.

Workup

  1. customThe reaction was then quenched by addition of 1M NaOH (aq.) (10 ml) and DCM (15 ml)
  2. customThe organic layer was separated
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customevaporated
  6. customPurification by column chromatography 5-10% MeOH

Sources & evidence

ORD record
ord-cfcee50861094aa1bfe4b029329f67d9
Source dataset
uspto-grants-2014_04
Patent number
US08710224B2

Reaction notes

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