Acetic Anhydride → HCID 178473794, compound

HRID 1297192Notes

Reaction equation

HRID 1297192 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[CH2:7][CH2:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[NH:20][C:19]3[CH:21]=[CH:22][C:23]([C:25]([NH2:27])=[O:26])=[CH:24][C:18]=3[N:17]=2)=[CH:12][CH:11]=1.[C:28](OC(=O)C)(=[O:30])[CH3:29]>CN(C)C1C=CN=CC=1.CN(C=O)C>[C:28]([N:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[CH2:7][CH2:8][O:9][C:10]1[CH:11]=[CH:12][C:13]([C:16]2[NH:20][C:19]3[CH:21]=[CH:22][C:23]([C:25]([NH2:27])=[O:26])=[CH:24][C:18]=3[N:17]=2)=[CH:14][CH:15]=1)(=[O:30])[CH3:29]

Participants

5

Reactant 2

HCID 7918Acetic Anhydride2×HCID 178513585HCID 178513585, compound

Product 1

HCID 178473794HCID 178473794, compoundYield 47%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalyst2×HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-[4-(2-piperidin-2-yl-ethoxy)-phenyl]-1H-benzoimidazole-5-carboxylic acid amide (75 mg, 0.21 mmol) and 4-(dimethylamino)pyridine (13 mg, 0.10 mmol) in DMF (0.5 mL) was added acetic anhydride (20 μL, 0.23 mmol). The reaction mixture was stirred for 18 h before additional acetic anhydride (1 equiv.) and DMAP (3 equiv.) were added. After an additional 24 h, HPLC monitoring indicated reaction completion. The crude material was purified by reverse phase HPLC (C18; H2O/CH3CN/0.01% TFA), providing 39 mg (47%) of product. HPLC (Method C): Rt=4.70. MS (ESI+): mass calcd. for C23H26N4O3, 406.20; m/z found, 407.3 [M+H]+. 1H NMR (400 MHz, CD3OD): 8.18 (s, 1H), 8.03-7.96 (m, 3H), 7.71 (d, J=8.6 Hz, 1H), 7.18 (d, J=9.0 Hz, 1H), 7.13 (d, J=9.0 Hz, 1H), 4.41-4.26 (m, 1H), 4.15-3.94 (m, 1H), 4.04-3.98 (m, 1H), 3.69-3.64 (m, 1H), 2.67-2.60 (m, 1H), 2.41-2.21 (m, 1H), 1.97 (s, 3H), 1.98-1.85 (m, 1H), 1.72-1.52 (m, 5H), 1.48-1.23 (m, 1H).

Workup

  1. additionwere added
  2. customreaction completion
  3. customThe crude material was purified by reverse phase HPLC (C18; H2O/CH3CN/0.01% TFA)

Sources & evidence

ORD record
ord-919a2b312b654babb2db880bc81396eb
Source dataset
uspto-grants-2007_07
Patent number
US07250427B2

Reaction notes

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