Acetic Anhydride → HCID 20801207, compound

HRID 1071678Notes

Reaction equation

HRID 1071678 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([NH:7][C:8]([C:10]2[N:11]([CH2:19][C:20]3[CH:24]=[C:23]([C:25]4[S:26][C:27]([Cl:30])=[CH:28][CH:29]=4)[O:22][N:21]=3)[C:12]3[C:17]([CH:18]=2)=[CH:16][CH:15]=[CH:14][CH:13]=3)=[O:9])[CH2:3][CH2:2]1.[C:31](OC(=O)C)(=[O:33])[CH3:32]>C(Cl)Cl.CCN(CC)CC>[C:31]([N:1]1[CH2:6][CH2:5][CH:4]([NH:7][C:8]([C:10]2[N:11]([CH2:19][C:20]3[CH:24]=[C:23]([C:25]4[S:26][C:27]([Cl:30])=[CH:28][CH:29]=4)[O:22][N:21]=3)[C:12]3[C:17]([CH:18]=2)=[CH:16][CH:15]=[CH:14][CH:13]=3)=[O:9])[CH2:3][CH2:2]1)(=[O:33])[CH3:32]

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 20801153HCID 20801153, compound

Product 1

HCID 20801207HCID 20801207, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

To a solution of 50 mg 1-[5-(5-Chloro-thiophen-2-yl)-isoxazol-3-ylmethyl]-1H-indole-2-carboxylic acid piperidin-4-ylamide in 2 ml DCM, 0.3 ml NEt3 and 11 mg acetic acid anhydride were added at RT and stirred over night. After removal of the solvent under reduced pressure the residue was directly purified by preparative RP-HPLC eluting with a gradient of 0-100% acetonitrile in water (+0.01% trifluoroacetic acid). After lyophilization the product was obtained as a white solid.

Workup

  1. customAfter removal of the solvent under reduced pressure the residue
  2. customwas directly purified by preparative RP-HPLC
  3. washeluting with a gradient of 0-100% acetonitrile in water (+0.01% trifluoroacetic acid)
  4. customAfter lyophilization the product was obtained as a white solid

Sources & evidence

ORD record
ord-040c88f5fcee417286728143072108a8
Source dataset
uspto-grants-2005_06
Patent number
US06906084B2

Reaction notes

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