HCID 10805283, compound → HCID 11524270, compound

HRID 133536Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:22])[C:4]1[CH:9]=[CH:8][C:7]([C:10]([C:12]2[C:13]3[CH2:21][CH2:20][CH2:19][CH2:18][C:14]=3[S:15][C:16]=2[NH2:17])=O)=[CH:6][CH:5]=1.[CH:23]1([C:26](=[O:31])[CH2:27][C:28](=O)[CH3:29])[CH2:25][CH2:24]1>C(O)(=O)C.S(=O)(=O)(O)O>[CH3:1][O:2][C:3](=[O:22])[C:4]1[CH:9]=[CH:8][C:7]([C:10]2[C:27]([C:26]([CH:23]3[CH2:25][CH2:24]3)=[O:31])=[C:28]([CH3:29])[N:17]=[C:16]3[S:15][C:14]4[CH2:18][CH2:19][CH2:20][CH2:21][C:13]=4[C:12]=23)=[CH:6][CH:5]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a stirred solution of 60 mg (0.19 mmol) 4-(2-Amino-4,5,6,7-tetrahydro-benzo[b]thiophene-3-carbonyl)-benzoic acid methyl ester in 2 ml acetic acid was added 32 mg (0.25 mmol) of 1-cyclopropyl-butane-1,3-dione and one drop of sulfuric acid. The mixture was then stirred at 100° C. for 10 minutes in a microwave and then concentrated in vacuo. Preparative HPLC (30% CH3CN/H20) afforded 28 mg (37%) 4-(3-cyclopropanecarbonyl-2-methyl-5,6,7,8-tetrahydro-benzo[4,5]thieno[2,3-b]pyridin-4-yl)-benzoic acid methyl ester as a light pink solid. ES-MS m/e (%): 406 (M+H+, 100).

Workup

concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-5168c5bd4ab14fe2bb93880dda6475f3
Source dataset: uspto-grants-2008_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07390903B2

Reaction notes

Loading…