Tetrahydrofuran → 4-[5-Bromo-6-(3-imidazol-1-yl-propylamino)-pyridine-3-sulfonyl]-5-methylsulfanyl-thiophene-2-carboxylic acid methyl ester

HRID 723114Notes

Reaction equation

[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([S:21][CH3:22])=[C:8]([S:10]([C:13]2[CH:14]=[N:15][C:16](Cl)=[C:17]([Br:19])[CH:18]=2)(=[O:12])=[O:11])[CH:9]=1)=[O:4].[N:23]1([CH2:28][CH2:29][CH2:30][NH2:31])[CH:27]=[CH:26][N:25]=[CH:24]1.C(N(C(C)C)CC)(C)C.C1COCC1>CN(C=O)C>[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([S:21][CH3:22])=[C:8]([S:10]([C:13]2[CH:14]=[N:15][C:16]([NH:31][CH2:30][CH2:29][CH2:28][N:23]3[CH:27]=[CH:26][N:25]=[CH:24]3)=[C:17]([Br:19])[CH:18]=2)(=[O:12])=[O:11])[CH:9]=1)=[O:4]

Participants

Conditions

Temperature: 80 °C

Procedure

To a vial containing a stirbar was added 4-(5-bromo-6-chloro-pyridine-3-sulfonyl)-5-methylsulfanyl-thiophene-2-carboxylic acid methyl ester (0.050 g, 0.113 mmol), (Example 2: step c), 3-imidazol-1-yl-propylamine (0.018 g, 0.146 mmol), diisopropylethylamine (0.073 g, 0.565 mmol), THF [0.50 mL], DMF [0.50 mL]. The reaction vessel was sealed and the solution was heated to 80° C. for 18 hours. Removal of the solvents in vacuo followed by chromatography (5% MeOH/DCM) yielded the title compound. 1H-NMR (CDCl3): δ 8.69 (d, 1H, J=2.1 Hz), 8.10 (d, 1H J=2.1 Hz), 8.03 (s, 1H), 8.02 (s, 1H), 7.57 (s, 1H), 7.10 (s, 1H), 6.97 (s 1H), 5.70 (t, 1H, J=5.8 Hz), 4.06 (t, 2H, J=6.8 Hz), 3.89 (s, 3H), 3.57 (m, 2H), 2.97 (s, 2H), 2.90 (s, 2H), 2.64 (s, 3H), 2.17 (m, 2H). ESI-MS (m/z): Calcd. For C18H19BrN4O4S3: 532.5 (M+H); found 530.9, 532.9.

Workup

additionTo a vial containing a stirbar
customThe reaction vessel was sealed
customRemoval of the solvents in vacuo

Sources & evidence

ORD record: ord-e5c848c820d44d59b4f5e55142506219
Source dataset: uspto-grants-2006_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07138530B2

Reaction notes

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