Ethyl orthoformate → HCID 44416841, compound

HRID 1353083Notes

Reaction equation

HRID 1353083 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:17][C:18]([C:20]2[CH:24]=[C:23]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[S:22][C:21]=2[NH2:31])=[O:19])[CH:6]=[CH:7][C:8]=1[O:9][CH2:10][CH2:11][N:12]1[CH2:16][CH2:15][CH2:14][CH2:13]1.[CH:32](OCC)(OCC)OCC>C1CCN2C(=NCCC2)CC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([N:17]2[C:18](=[O:19])[C:20]3[CH:24]=[C:23]([C:25]4[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=4)[S:22][C:21]=3[N:31]=[CH:32]2)[CH:6]=[CH:7][C:8]=1[O:9][CH2:10][CH2:11][N:12]1[CH2:16][CH2:15][CH2:14][CH2:13]1

Participants

4

Reactant 2

HCID 31214Ethyl orthoformateHCID 86597114HCID 86597114, compound

Product 1

HCID 44416841HCID 44416841, compound

Reagents, catalysts & solvents 1

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneCatalyst

Procedure

2-Amino-5-phenyl-thiophene-3-carboxylic acid [3-methoxy-4-(2-pyrrolidin-1-yl-ethoxy)phenyl]-amide [Example E1] (28 mg, 0.064 mmol) was stirred at 95° C. in triethyl orthoformate (5 ml) for 24 h. The mixture was cooled, 4 drops of DBU added and the volatiles removed. The crude product was purified by chromatography on silica gel (eluting with dichloromethane-methanol-aq. ammonia) to give the title compound.

Workup

  1. temperatureThe mixture was cooled
  2. customthe volatiles removed
  3. customThe crude product was purified by chromatography on silica gel (eluting with dichloromethane-methanol-aq. ammonia)

Sources & evidence

ORD record
ord-f99ed3ae44604e68a6b703b3d38c21a1
Source dataset
uspto-grants-2007_05
Patent number
US07220777B2

Reaction notes

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