Trimethyl orthoformate → HCID 178505723, compound

HRID 250765Notes

Reaction equation

HRID 250765 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[C:9]1[NH:10][C:11]([C:20]2[CH:25]=[CH:24][C:23]([NH2:26])=[C:22]([NH:27][CH2:28][CH:29]3[CH2:31][CH2:30]3)[CH:21]=2)=[C:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[N:13]=1.[CH3:32]OC(OC)OC>C(O)(=O)C>[CH:29]1([CH2:28][N:27]2[C:22]3[CH:21]=[C:20]([C:11]4[NH:10][C:9]([C:3]5[C:4]([F:8])=[CH:5][CH:6]=[CH:7][C:2]=5[F:1])=[N:13][C:12]=4[C:14]4[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=4)[CH:25]=[CH:24][C:23]=3[N:26]=[CH:32]2)[CH2:30][CH2:31]1

Participants

4

Reactant 2

HCID 9005Trimethyl orthoformateHCID 178507460HCID 178507460, compound

Product 1

HCID 178505723HCID 178505723, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Heat a mixture of 2-(2,6-difluorophenyl)-4-phenyl-5-(3-(cyclopropylmethyl)amino-4-aminophenyl)imidazole (0.100 g, 0.24 mmol) and trimethylorthoformate (2 mL) in acetic acid (4 mL) at 120° C. for 1 hour. Cool the reaction mixture to room temperature and concentrate under reduced pressure. Dilute the residue with methanol and pour over an SCX column, eluting sequentially with methanol followed by 2N ammonia in methanol. Combine the basic fractions and concentrate under reduced pressure. Subject the residue to silica gel chromatography, eluting with 95:5 dichloromethane:methanol to provide the title compound as a white solid.

Workup

  1. temperatureHeat
  2. concentrationconcentrate under reduced pressure
  3. additionDilute the residue with methanol
  4. additionpour over an SCX column
  5. washeluting sequentially with methanol
  6. concentrationconcentrate under reduced pressure
  7. washeluting with 95:5 dichloromethane

Sources & evidence

ORD record
ord-169e2c8024ae4569a492af4f91878655
Source dataset
uspto-grants-2011_01
Patent number
US07863310B2

Reaction notes

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