Trifluoroacetic acid → HCID 22256616, compound

HRID 1611549Notes

Reaction equation

HRID 1611549 reaction equation
[C:1]([C:3]1[C:4]([NH:21][C:22]2[CH:27]=[C:26]([O:28][CH3:29])[C:25]([Cl:30])=[CH:24][C:23]=2[Cl:31])=[C:5]2[S:11][C:10](/[CH:12]=[CH:13]/[C:14]([O:16]C(C)(C)C)=[O:15])=[CH:9][C:6]2=[N:7][CH:8]=1)#[N:2].FC(F)(F)C(O)=O>ClCCl>[C:1]([C:3]1[C:4]([NH:21][C:22]2[CH:27]=[C:26]([O:28][CH3:29])[C:25]([Cl:30])=[CH:24][C:23]=2[Cl:31])=[C:5]2[S:11][C:10](/[CH:12]=[CH:13]/[C:14]([OH:16])=[O:15])=[CH:9][C:6]2=[N:7][CH:8]=1)#[N:2]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 10344894HCID 10344894, compound

Product 1

HCID 22256616HCID 22256616, compoundYield 92.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of tert-butyl (2E)-3-{6-cyano-7-[(2,4-dichloro-5-methoxyphenyl)amino]thieno[3,2-b]pyridine-2yl)prop-2-enoate (910.8 mg, 1.91 mmol), trifluoroacetic acid (2.18 g, 19.1 mmol) in 27 mL of dichloromethane is stirred at room temperature for 3 days, then concentrated in vacuo. The residue is triturated with ether to provide 741 mg of (2E)-3-(6-cyano-7-[(2,4-dichloro-5-methoxyphenyl)amino]thieno[3,2-b]pyridin-2-yl)prop-2-enoic acid as a beige solid, mp>250° C.; 1H NMR (DMSO-d6) δ 3.84 (s, 3H), 6.28 (d, J=16 Hz, 1H), 7.38 (s, 1H), 7.70-7.88 (m, 2H), 7.90 (s, 1H), 8.62 (s, 1H), 9.81 (s, 1H), 12.50 (s, 1H); MS 420.1, 422.0 (M+H)+.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue is triturated with ether

Sources & evidence

ORD record
ord-79cf2b68b1cc4545a8433695ada9b39a
Source dataset
uspto-grants-2006_01
Patent number
US06987116B2

Reaction notes

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