Ethyl orthoformate → HCID 68313393, compound

HRID 1843126Notes

Reaction equation

HRID 1843126 reaction equation
O=[C:2]1[NH:10][C:9]2[C:4](=[N:5][C:6]([C:11]3[CH:12]=[N:13][N:14]4[CH:19]=[CH:18][C:17]([C:20]#[N:21])=[CH:16][C:15]=34)=[N:7][CH:8]=2)[N:3]1[CH:22]1[CH2:27][CH2:26][O:25][CH2:24][CH2:23]1.C(OC(OCC)OCC)C>CCO>[O:25]1[CH2:24][CH2:23][CH:22]([N:3]2[CH:2]=[N:10][C:9]3[C:4]2=[N:5][C:6]([C:11]2[CH:12]=[N:13][N:14]4[CH:19]=[CH:18][C:17]([C:20]#[N:21])=[CH:16][C:15]=24)=[N:7][CH:8]=3)[CH2:27][CH2:26]1

Participants

4

Reactant 2

HCID 31214Ethyl orthoformateHCID 52933409HCID 52933409, compound

Product 1

HCID 68313393HCID 68313393, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
123 °C

Procedure

To a suspension of the compound obtained in example 1 section d (100 mg, 0.30 mmol) in EtOH (1 mL), PTSA monohydrate (5.7 mg, 0.03 mmol) and triethylorthoformate (1 mL) were added. The reaction mixture was heated in a CEM Explorer microwave oven at 123° C. and 270 W for 30 min. Then, it was evaporated to dryness. The crude product thus obtained was chromatographed over silica gel using MeOH/EtOAc mixtures of increasing polarity as eluent, to afford 81 mg of the desired compound (79% yield).

Workup

  1. customThen, it was evaporated to dryness
  2. customThe crude product thus obtained
  3. customwas chromatographed over silica gel
  4. temperatureof increasing polarity as eluent

Sources & evidence

ORD record
ord-d21c0fb7589a46f1a6fa45e6cc881c72
Source dataset
uspto-grants-2015_02
Patent number
US08946257B2

Reaction notes

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