Formic Acid → HCID 25022847, compound

HRID 1437119Notes

Reaction equation

HRID 1437119 reaction equation
[C:1]([O:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([Cl:15])[C:10]=1[NH:16][C:17]([C:19]1[S:23][C:22]([NH:24]C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=[N:21][CH:20]=1)=[O:18])(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3].C(O)=O>CCO>[C:1]([O:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([Cl:15])[C:10]=1[NH:16][C:17]([C:19]1[S:23][C:22]([NH2:24])=[N:21][CH:20]=1)=[O:18])(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3]

Participants

4

Reactant 2

HCID 284Formic AcidHCID 250228462,2-Dimethyl-propanoic Acid [3-Chloro-2-[[[2-[(triphenylmethyl)amino]-5-thiazolyl]carbonyl]amino]phenyl]methyl Ester

Product 1

HCID 25022847HCID 25022847, compoundYield 87.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of compound 9a (8.90 g, 14 mmol) and formic acid (15 mL, 96% in H2O) in EtOH (150 mL) was refluxed for 24 h. After cooling, the solution was concentrated in vacuo. The residue was subjected to a short column using EtOAc in hexane (30% to 70%) to give the crude compound 10a which was triturated with 10% EtOAc in hexane to give compound 10a (4.50 g, 87% yield). 1H NMR (500 MHz, CDCl3) δ 1.17 (s, 9H), 5.09 (s, 2H), 7.20-7.39 (m, 5H), 8.01 (s, 1H), 8.84 (s, 1H).

Workup

  1. temperaturewas refluxed for 24 h
  2. temperatureAfter cooling
  3. concentrationthe solution was concentrated in vacuo
  4. customto give the crude compound 10a which
  5. customwas triturated with 10% EtOAc in hexane

Sources & evidence

ORD record
ord-50da69ef0df048c09adb0646ee47fb09
Source dataset
uspto-grants-2009_11
Patent number
US07622473B2

Reaction notes

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