Acetic Acid → HCID 18367980, compound

HRID 379910Notes

Reaction equation

HRID 379910 reaction equation
[Si]([O:8][CH2:9][C:10]1[C:11]([C:16]([C:18]2[NH:19][C:20]3[C:25]([C:26]=2[NH:27][C:28](=[O:31])[CH2:29][CH3:30])=[CH:24][CH:23]=[C:22]([Cl:32])[CH:21]=3)=[O:17])=[N:12][CH:13]=[CH:14][CH:15]=1)(C(C)(C)C)(C)C.C(O)(=O)C.[F-].C([NH3+])CCC.C([NH3+])CCC.C([NH3+])CCC.C([NH3+])CCC.[F-].[F-].[F-]>C1COCC1.C(OCC)C>[Cl:32][C:22]1[CH:21]=[C:20]2[C:25]([C:26]([NH:27][C:28](=[O:31])[CH2:29][CH3:30])=[C:18]([C:16]([C:11]3[C:10]([CH2:9][OH:8])=[CH:15][CH:14]=[CH:13][N:12]=3)=[O:17])[NH:19]2)=[CH:24][CH:23]=1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 18367802HCID 18367802, compoundHCID 18367810HCID 18367810, compound

Product 1

HCID 18367980HCID 18367980, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-[(3-tert-butyldimethylsilyloxymethyl)pyridine-2-carbonyl]-6-chloro-3-(propionylamino)indole (step 5, 544 mg, 1.15 mmol) and acetic acid (0.20 ml, 3.50 mmol) in THF (30 ml) was added tetra(n-butylammonium)fluoride (1M in THF, 3.5 ml, 3.50 mmol) at 0° C. The mixture was stirred for 4.5 h at the same temperature and diluted with diethyl ether (200 ml). This solution was washed with saturated aqueous sodium bicarbonate (50 ml), water (50 ml×2), and dried (MgSO4). Removal of solvent gave a crystalline residue. Recrystallization from ethyl acetate afforded 361 mg (88%) of the title compound. m.p.: 198-199° C. IR (KBr) ν: 3250, 1663, 1624, 1607, 1578, 1541, 1472, 1352, 1211, 1178, 1153, 1074, 1045, 1013, 833, 808, 716 cm−1 1H-NMR (CDCl3) δ: 11.33 (1 H, br s), 10.74 (1 H, br s), 8.75 (1 H, dd, J=1.6, 4.8 Hz), 8.47 (1 H, d, J=9.1 Hz), 8.00 (1 H, dd, J=1.5, 7.7 Hz), 7.57 (1 H, dd, J=4.8, 7.7 Hz), 7.36 (1 H, d, J=1.8 Hz), 7.05 (1 H, dd, J=1.8 and 9.1 Hz), 4.87 (2 H, d, J=7.3 Hz), 4.00 (1 H, t, J=7.1 Hz), 2.62 (2 H, q, J=7.6 Hz), 1.36 (3 H, t, J=7.6 Hz).

Workup

  1. washThis solution was washed with saturated aqueous sodium bicarbonate (50 ml), water (50 ml×2)
  2. dry with materialdried (MgSO4)
  3. customRemoval of solvent
  4. customgave a crystalline residue
  5. customRecrystallization from ethyl acetate

Sources & evidence

ORD record
ord-bfb97144cf1d4956a1ad8fed2756d8e9
Source dataset
uspto-grants-2001_10
Patent number
US06300363B1

Reaction notes

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