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 2358865Notes

Reaction equation

HRID 2358865 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-3a54ddb796144725a35cf7772c5af1a1
Source dataset
uspto-grants-2010_07
Patent number
US07763729B2

Reaction notes

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