Ammonia → 3-[(2-Cyanophenyl)amino]-6-oxo-7-(3-thienyl)-6,7-dihydrothieno[2,3-b]pyridine-2-carboxamide

HRID 30430Notes

Reaction equation

HRID 30430 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[NH:9][C:10]1[C:18]2[CH:17]=[CH:16][C:15](=[O:19])[N:14]([C:20]3[CH:24]=[CH:23][S:22][CH:21]=3)[C:13]=2[S:12][C:11]=1[C:25]([O:27]CC)=O)#[N:2].C(OCCO)C.[NH3:36]>>[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[NH:9][C:10]1[C:18]2[CH:17]=[CH:16][C:15](=[O:19])[N:14]([C:20]3[CH:24]=[CH:23][S:22][CH:21]=3)[C:13]=2[S:12][C:11]=1[C:25]([NH2:36])=[O:27])#[N:2]

Participants

4

Reactant 3

HCID 222AmmoniaHCID 8076Glycol monoethyl etherHCID 68454063HCID 68454063, compound

Product 1

HCID 684549973-[(2-Cyanophenyl)amino]-6-oxo-7-(3-thienyl)-6,7-dihydrothieno[2,3-b]pyridine-2-carboxamide

Conditions

Temperature
80 °C

Procedure

A mixture of Example 66 (100 mg), 2-ethoxyethanol and liquid ammonia was placed in a sealed pressure vessel and heated at 80° C. and 400 psi for 48 h. The volatiles were removed in vacuo and the residue purified by column chromatography (silica, EtOAc) to give the title compound (30 mg). δH (CDCl3) 7.59-7.46 (4H, m), 7.28-7.21 (3H, m), 7.20 (1H, t, J 2.0 Hz), 7.01 (1H, d, J 8.3 Hz), 6.49 (1H, d, J 9.7 Hz), 5.55 (2H, br s). LCMS (ES+) RT 2.845 minutes, 392.9 (M+H)+

Workup

  1. customThe volatiles were removed in vacuo
  2. customthe residue purified by column chromatography (silica, EtOAc)

Sources & evidence

ORD record
ord-cda9ed844bfe4417b80bbaeb2574e8fb
Source dataset
uspto-grants-2008_09
Patent number
US07423047B2

Reaction notes

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