Ethyl orthoformate → HCID 17989373, compound

HRID 1353066Notes

Reaction equation

HRID 1353066 reaction equation
[NH2:1][C:2]1[CH:26]=[C:25]([O:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH:24]=[CH:23][C:3]=1[C:4]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][CH2:15][N:16]2[CH2:20][CH2:19][CH2:18][CH2:17]2)=[C:9]([O:21][CH3:22])[CH:8]=1)=[O:5].[CH2:34](OC(OCC)OCC)C.C1CCN2C(=NCCC2)CC1>ClCCCl>[CH3:22][O:21][C:9]1[CH:8]=[C:7]([N:6]2[C:4](=[O:5])[C:3]3[C:2](=[CH:26][C:25]([O:27][C:28]4[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=4)=[CH:24][CH:23]=3)[N:1]=[CH:34]2)[CH:12]=[CH:11][C:10]=1[O:13][CH2:14][CH2:15][N:16]1[CH2:17][CH2:18][CH2:19][CH2:20]1

Participants

5

Reactant 3

HCID 31214Ethyl orthoformateHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 21101396HCID 21101396, compound

Product 1

HCID 17989373HCID 17989373, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

2-Amino-N-[3-methoxy-4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-4-phenoxy-benzamide [Example C1] (50 mg, 0.11 mmol) was dissolved in 1,2-dichloroethane (5 ml) and treated with triethylorthoformate [Aldrich] (2 ml) then heated to reflux for 12 h. The mixture was cooled and DBU (0.1 ml) introduced. The solvent was evaporated then the residue purified by flash chromatography on silica gel (eluting with ammonia-methanol-dichloromethane) to obtain the title compound;

Workup

  1. temperaturethen heated
  2. temperatureto reflux for 12 h
  3. temperatureThe mixture was cooled
  4. customThe solvent was evaporated
  5. customthe residue purified by flash chromatography on silica gel (eluting with ammonia-methanol-dichloromethane)

Sources & evidence

ORD record
ord-f42730ba7b094a11bb032a094b719ab6
Source dataset
uspto-grants-2007_05
Patent number
US07220777B2

Reaction notes

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