Acetic Anhydride → 4-{5-[4-(4-acetyl-piperazine-1-carbonyl)-phenyl]-1H-pyrrolo[2,3-b]pyridin-3-yl}-benzamide

HRID 333178Notes

Reaction equation

HRID 333178 reaction equation
Cl.[N:2]1([C:8]([C:10]2[CH:15]=[CH:14][C:13]([C:16]3[CH:17]=[C:18]4[C:24]([C:25]5[CH:33]=[CH:32][C:28]([C:29]([NH2:31])=[O:30])=[CH:27][CH:26]=5)=[CH:23][NH:22][C:19]4=[N:20][CH:21]=3)=[CH:12][CH:11]=2)=[O:9])[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.C(N(CC)CC)C.[C:41](OC(=O)C)(=[O:43])[CH3:42].CCOC(C)=O>CO>[C:41]([N:5]1[CH2:4][CH2:3][N:2]([C:8]([C:10]2[CH:15]=[CH:14][C:13]([C:16]3[CH:17]=[C:18]4[C:24]([C:25]5[CH:26]=[CH:27][C:28]([C:29]([NH2:31])=[O:30])=[CH:32][CH:33]=5)=[CH:23][NH:22][C:19]4=[N:20][CH:21]=3)=[CH:12][CH:11]=2)=[O:9])[CH2:7][CH2:6]1)(=[O:43])[CH3:42]

Participants

6

Reactant 4

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 1317319134-{5-[4-(piperazine-1-carbonyl)-phenyl]-1H-pyrrolo[2,3-b]pyridin-3-yl}-benzamide, hydrochloride salt

Product 1

HCID 667791694-{5-[4-(4-acetyl-piperazine-1-carbonyl)-phenyl]-1H-pyrrolo[2,3-b]pyridin-3-yl}-benzamideYield 25%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 4-{5-[4-(piperazine-1-carbonyl)-phenyl]-1H-pyrrolo[2,3-b]pyridin-3-yl}-benzamide, hydrochloride salt (19 mg, 0.041 mmol) in MeOH (2 ml) was added triethylamine (400 μl, 2.88 mmol) and acetic anhydride (100 μl, 1.06 mmol). The mixture was stirred for 1 hr at room temperature. EtOAc was added and washed with saturated aqu. NaHCO3, water, brine and dried and evacuated. Purification on silica gel employing 0-10% MeOH:DCM provided 4.7 mg (25%) of the title compound. MS ESI (m/z): 468.3 (M+1)+, calc. 467.

Workup

  1. washwashed with saturated aqu
  2. dry with materialNaHCO3, water, brine and dried
  3. customevacuated
  4. customPurification on silica gel employing 0-10% MeOH

Sources & evidence

ORD record
ord-03168a96f1be404d838c1852f906f25b
Source dataset
uspto-grants-2014_11
Patent number
US08877772B2

Reaction notes

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