Ethyl orthoformate → HCID 178428314, compound

HRID 1626907Notes

Reaction equation

HRID 1626907 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:9]([CH3:31])[C:10]([NH:12][CH2:13][C:14]2[C:15]([N:24]3[CH2:29][CH2:28][CH:27]([CH3:30])[CH2:26][CH2:25]3)=[N:16][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:18][CH:19]=2)=[O:11])[CH:5]=[CH:6][C:7]=1[NH2:8].[CH:32](OCC)(OCC)OCC>O>[NH:8]1[C:7]2[CH:6]=[CH:5][C:4]([CH:9]([CH3:31])[C:10]([NH:12][CH2:13][C:14]3[C:15]([N:24]4[CH2:25][CH2:26][CH:27]([CH3:30])[CH2:28][CH2:29]4)=[N:16][C:17]([C:20]([F:23])([F:21])[F:22])=[CH:18][CH:19]=3)=[O:11])=[CH:3][C:2]=2[N:1]=[CH:32]1

Participants

4

Reactant 2

HCID 31214Ethyl orthoformateHCID 25124036HCID 25124036, compound

Product 1

HCID 178428314HCID 178428314, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2-(3,4-diaminophenyl)-N-(4-methyl-6′-trifluoromethyl-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-3′-ylmethyl)-propionamide (48 mg, 0.110 mmol) was combined at RT with triethyl orthoformate (2 ml). The reaction mixture was heated to reflux for 2 h and cooled to RT. The reaction mixture was combined with water and repeatedly extracted with DCM. The combined organic phases were dried over MgSO4 and filtered. The solvent was removed under a vacuum and the residue purified by means of column chromatography (DCM/MeOH=10:1).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 2 h
  3. extractionrepeatedly extracted with DCM
  4. dry with materialThe combined organic phases were dried over MgSO4
  5. filtrationfiltered
  6. customThe solvent was removed under a vacuum
  7. customthe residue purified by means of column chromatography (DCM/MeOH=10:1)

Sources & evidence

ORD record
ord-ea1adaddbfb44fe98b51aab885530ce0
Source dataset
uspto-grants-2014_07
Patent number
US08785474B2

Reaction notes

Loading…