2-Amino-2-methyl-1-propanol → 3-Anilino-n-(2-hydroxy-1,1-dimethylethyl)-6-oxo-7-phenyl-6,7-dihydrothieno[2,3-b]pyridine-2-carboxamide

HRID 30433

Reaction equation

HRID 30433 reaction equation
[C:1]1([NH:7][C:8]2[C:16]3[CH:15]=[CH:14][C:13](=[O:17])[N:12]([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)[C:11]=3[S:10][C:9]=2[C:24](OCC)=[O:25])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:29][C:30]([CH3:34])([CH3:33])[CH2:31][OH:32]>>[NH:7]([C:8]1[C:16]2[CH:15]=[CH:14][C:13](=[O:17])[N:12]([C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)[C:11]=2[S:10][C:9]=1[C:24]([NH:29][C:30]([CH3:34])([CH3:33])[CH2:31][OH:32])=[O:25])[C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

3

Reactant 2

HCID 118072-Amino-2-methyl-1-propanolHCID 9865198Ethyl 3-(phenylamino)-6-oxo-7-phenyl-6,7-dihydrothieno[2,3-b]pyridine-2-carboxylate

Product 1

HCID 684567053-Anilino-n-(2-hydroxy-1,1-dimethylethyl)-6-oxo-7-phenyl-6,7-dihydrothieno[2,3-b]pyridine-2-carboxamideYield 16%

Procedure

A mixture of Example 1 and 2-amino-2-methyl-1-propanol (1.22 mL, 13 mmol) was heated at 150° C. for 16 h. The mixture was partitioned between DCM (60 mL) and 10% citric acid (75 mL). The aqueous phase was extracted with DCM (20 mL). The combined organics were dried (Na2SO4) and concentrated in vacuo. Purification by column chromatography (silica, 40% EtOAc in DCM) gave the title compound as a pale brown solid (45 mg, 16%). δH (CDCl3) 8.44 (1H, br s), 7.56-7.46 (3H, m), 7.34-7.31 (2H, m), 7.26-7.20 (3H, m), 7.03-6.96 (3H, m), 6.33 (1H, d, J 9.7 Hz), 5.65 (1H, br s), 4.21-4.18 (1H, br m), 3.49 (2H, d, J 5.5 Hz), 1.18 (6H, s). LCMS (ES+) 434 (M+H)+.

Workup

  1. customThe mixture was partitioned between DCM (60 mL) and 10% citric acid (75 mL)
  2. extractionThe aqueous phase was extracted with DCM (20 mL)
  3. dry with materialThe combined organics were dried (Na2SO4)
  4. concentrationconcentrated in vacuo
  5. customPurification by column chromatography (silica, 40% EtOAc in DCM)

Sources & evidence

ORD record
ord-7602cf148da24a8683ae94a7291722d7
Source dataset
uspto-grants-2008_09
Patent number
US07423047B2

Linked notes

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