Tetrahydrofuran → 6-(cis-2-(Tert-butoxycarbonylamino)cyclohexylamino)-5-fluoro-2-(isoquinoline 4-ylamino)nicotinic acid

HRID 1620116Notes

Reaction equation

[OH-].[Na+].O1CCCC1.[C:8]([O:12][C:13]([NH:15][C@H:16]1[CH2:21][CH2:20][CH2:19][CH2:18][C@H:17]1[NH:22][C:23]1[C:32]([F:33])=[CH:31][C:26]([C:27]([O:29]C)=[O:28])=[C:25]([NH:34][C:35]2[C:44]3[C:39](=[CH:40][CH:41]=[CH:42][CH:43]=3)[CH:38]=[N:37][CH:36]=2)[N:24]=1)=[O:14])([CH3:11])([CH3:10])[CH3:9]>CO>[C:8]([O:12][C:13]([NH:15][C@H:16]1[CH2:21][CH2:20][CH2:19][CH2:18][C@H:17]1[NH:22][C:23]1[C:32]([F:33])=[CH:31][C:26]([C:27]([OH:29])=[O:28])=[C:25]([NH:34][C:35]2[C:44]3[C:39](=[CH:40][CH:41]=[CH:42][CH:43]=3)[CH:38]=[N:37][CH:36]=2)[N:24]=1)=[O:14])([CH3:11])([CH3:9])[CH3:10]

Participants

Conditions

Temperature: 65 °C

Procedure

A 1N sodium hydroxide aqueous solution (2 ml) was added to a solution of tetrahydrofuran (2 ml) and methanol (2 ml) containing methyl 6-(cis-2-(tert-butoxycarbonylamino)cyclohexylamino)-5-fluoro-2-(isoquinoline 4-ylamino)nicotinate (75 mg), followed by stirring at 65° C. for 2 hours. The reaction mixture was cooled to room temperature, and the solvent was distilled away under reduced pressure. A saturated aqueous ammonium chloride solution was added to the obtained residue, solid matter was collected by filtration and washed with water and ethyl acetate, and a yellow solid of 6-(cis-2-(tert-butoxycarbonylamino)cyclohexylamino)-5-fluoro-2-(isoquinoline 4-ylamino)nicotinic acid (67 mg) was thus obtained.

Workup

temperatureThe reaction mixture was cooled to room temperature
distillationthe solvent was distilled away under reduced pressure
additionA saturated aqueous ammonium chloride solution was added to the obtained residue, solid matter
filtrationwas collected by filtration
washwashed with water and ethyl acetate

Sources & evidence

ORD record: ord-a6f4a24fafb3425d986a02cc3aad3b0b
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08772320B2

Reaction notes

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