Sodium → HCID 68095262, compound

HRID 1502341Notes

Reaction equation

[Na].[CH:2]([C:4]1[N:9]=[CH:8][C:7]([C:10]2[CH:19]=[C:18]3[C:13]([CH:14]=[C:15]([NH:20][C:21]([CH:23]4[CH2:25][CH2:24]4)=[O:22])[N:16]=[CH:17]3)=[CH:12][CH:11]=2)=[C:6]([CH3:26])[CH:5]=1)=[O:3]>O1CCCC1>[OH:3][CH2:2][C:4]1[N:9]=[CH:8][C:7]([C:10]2[CH:19]=[C:18]3[C:13]([CH:14]=[C:15]([NH:20][C:21]([CH:23]4[CH2:25][CH2:24]4)=[O:22])[N:16]=[CH:17]3)=[CH:12][CH:11]=2)=[C:6]([CH3:26])[CH:5]=1

Participants

Conditions

Temperature: 0 °C

Procedure

Sodium tertrahydroborate (10 mg, 0.27 mmol) was added to a solution of N-(7-(6-formyl-4-methylpyridin-3-yl)isoquinolin-3-yl)cyclopropanecarboxamide (45 mg, 0.14 mmol) in tetrahydrofuran (0.8 mL) cooled at 0° C. After 15 minutes, the reaction mixture was quenched with a few drops of water, diluted ethyl acetate (50 mL) and washed with water (50 mL). The organic layer was separated, dried over sodium sulfate, filtered, and evaporated in vacuo to afford a residue that was purified by reverse phase HPLC (5-85% acetonitrile in water with 0.1% formic acid over 14 min) to afford the title compound as an off-white solid (26 mg, 60%). 1H NMR (400 MHz, DMSO) δ 10.92 (s, 1H), 9.14 (s, 1H), 8.51 (s, 1H), 8.48 (d, J=5.0 Hz, 1H), 7.94 (m, 2H), 7.56 (d, J=8.5 Hz, 1H), 7.33 (d, J=5.0 Hz, 1H), 4.85 (t, J=5.3 Hz, 1H), 4.25 (d, J=5.2 Hz, 2H), 2.08 (m, 4H), 0.85 (m, 4H). LCMS (Method H): RT=2.40 min, M+H+=334.1.

Workup

customthe reaction mixture was quenched with a few drops of water, diluted ethyl acetate (50 mL)
washwashed with water (50 mL)
customThe organic layer was separated
dry with materialdried over sodium sulfate
filtrationfiltered
customevaporated in vacuo
customto afford a residue that
customwas purified by reverse phase HPLC (5-85% acetonitrile in water with 0.1% formic acid over 14 min)

Sources & evidence

ORD record: ord-c62b63b0cd3240098168fd2193857c9c
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09206175B2

Reaction notes

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