Methanol → HCID 9851727, compound

HRID 564750Notes

Reaction equation

[CH2:1]([O:3][C:4]([C:6]1[C:11]2=[CH:12][S:13][C:14]([NH2:15])=[C:10]2[C:9](=[O:16])[N:8]([C:17]2[CH:22]=[CH:21][C:20]([C:23]([OH:25])=O)=[CH:19][CH:18]=2)[N:7]=1)=[O:5])[CH3:2].[CH:26]([NH2:29])([CH3:28])[CH3:27].[CH:30](=[O:35])[CH2:31][CH2:32][CH2:33][CH3:34].[CH2:36]([N+:43]#[C-])[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1.[CH3:45]O>O1CCCC1>[CH2:1]([O:3][C:4]([C:6]1[C:11]2=[CH:12][S:13][C:14]([NH2:15])=[C:10]2[C:9](=[O:16])[N:8]([C:17]2[CH:22]=[CH:21][C:20]([C:23](=[O:25])[N:29]([CH:31]([C:30](=[O:35])[NH:43][CH2:36][C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)[CH2:32][CH2:33][CH2:34][CH3:45])[CH:26]([CH3:28])[CH3:27])=[CH:19][CH:18]=2)[N:7]=1)=[O:5])[CH3:2]

Participants

Conditions

Temperature: 45 °C

Procedure

To a solution of 5-amino-3-(4-carboxy-phenyl)-4-oxo-3,4-dihydro-thieno[3,4-d]pyridazine-1-carboxylic acid ethyl ester (9.0 mg, 0.025 mmol) in a mixture of methanol and tetrahydrofuran (200 ml, 1:1) was added isopropyl amine (25 μl, 0.025 mmol, 1.0 M in tetrahydrofuran), valeraldehyde (25 μl, 0.025 mmol, 1.0 M in tetrahydrofuran) and benzyl isocyanide (25 μl, 0.025 mmol, 1.0 M in tetrahydrofuran). The mixture was stirred at 45° C. for 64 h. After dilution with dichloromethane (1 ml), the mixture was purified on a preparative TLC plate using a mixture of methanol/ethyl acetate/hexane (1:4:4) as eluent. Spot eluting with Rf=0.66 was collected which afforded 6.3 mg (42%) of the title compound.

Workup

customAfter dilution with dichloromethane (1 ml), the mixture was purified on a preparative TLC plate
additiona mixture of methanol/ethyl acetate/hexane (1:4:4) as eluent
washSpot eluting with Rf=0.66
customwas collected which

Sources & evidence

ORD record: ord-2b967cddcd8747e7bf112232d53c171e
Source dataset: uspto-grants-2001_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06169087A

Reaction notes

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