Sodium Nitrite → HCID 59253043, compound

HRID 884764Notes

Reaction equation

[CH:1]1([C@H:4]([NH:11][C:12]([C:14]2[C:23]3[C:18](=[C:19](F)[CH:20]=[CH:21][CH:22]=3)[C:17](=[O:25])[N:16]([NH:26][CH2:27][CH3:28])[C:15]=2[CH3:29])=[O:13])[C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH2:3][CH2:2]1.N([O-])=[O:31].[Na+]>CN(C)C=O>[CH:1]1([C@H:4]([NH:11][C:12]([C:14]2[C:23]3[C:18](=[C:19]([OH:31])[CH:20]=[CH:21][CH:22]=3)[C:17](=[O:25])[N:16]([NH:26][CH2:27][CH3:28])[C:15]=2[CH3:29])=[O:13])[C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH2:3][CH2:2]1

Participants

Conditions

Temperature: 220 °C

Procedure

A mixture of 2-ethylamino-8-fluoro-3-methyl-1-oxo-1,2-dihydro-isoquinoline-4-carboxylic acid ((S)-cyclopropyl-phenyl-methyl)-amide (47.0 mg, 0.119 mmol, sodium nitrite (80.0 mg, 1.16 mmol), and N,N-dimethylformamide (0.2 mL) was heated under microwave irradiation at 220° C. for 60 min. Partitioned between EtOAc and water (4×10 ml), then combined aqueous phases were extracted with ether (15 ml), which was washed with water (4×10 ml). The combined organic solution was concentrated in vacuo, and purified by flash chromatography (with a gradient of heptane-ethylacetate) to give 2-ethylamino-8-hydroxy-3-methyl-1-oxo-1,2-dihydro-isoquinoline-4-carboxylic acid ((S)-cyclopropyl-phenyl-methyl)-amide as a yellow solid.

Workup

customPartitioned between EtOAc and water (4×10 ml)
extractioncombined aqueous phases were extracted with ether (15 ml), which
washwas washed with water (4×10 ml)
concentrationThe combined organic solution was concentrated in vacuo
custompurified by flash chromatography (with a gradient of heptane-ethylacetate)

Sources & evidence

ORD record: ord-25cba9652d7c4ead8a0b143c1ac1e30c
Source dataset: uspto-grants-2012_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08242134B2

Reaction notes

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