Sodium borohydride → 1-(2,2-Difluorobenzo[d][1,3]dioxol-5-yl)-n-(6-(1-(2-hydroxyethyl)-5-methyl-2-oxo-1,2-dihydropyridin-3-yl)-5-methylpyridin-2-yl)cyclopropanecarboxamide

HRID 869934Notes

Reaction equation

[F:1][C:2]1([F:37])[O:6][C:5]2[CH:7]=[CH:8][C:9]([C:11]3([C:14]([NH:16][C:17]4[N:22]=[C:21]([C:23]5[C:24](=[O:35])[N:25]([CH2:30][C:31](OC)=[O:32])[CH:26]=[C:27]([CH3:29])[CH:28]=5)[C:20]([CH3:36])=[CH:19][CH:18]=4)=[O:15])[CH2:13][CH2:12]3)=[CH:10][C:4]=2[O:3]1.[BH4-].[Na+]>C1COCC1>[F:37][C:2]1([F:1])[O:6][C:5]2[CH:7]=[CH:8][C:9]([C:11]3([C:14]([NH:16][C:17]4[CH:18]=[CH:19][C:20]([CH3:36])=[C:21]([C:23]5[C:24](=[O:35])[N:25]([CH2:30][CH2:31][OH:32])[CH:26]=[C:27]([CH3:29])[CH:28]=5)[N:22]=4)=[O:15])[CH2:12][CH2:13]3)=[CH:10][C:4]=2[O:3]1

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of methyl 2-(3-(6-(1-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)cyclopropanecarboxamido)-3-methylpyridin-2-yl)-5-methyl-2-oxopyridin-1(2H)-yl)acetate (17 mg, 0.034 mmol) in THF (1.6 mL) was added NaBH4 (7 mg, 0.17 mmol) and stirred at 50° C. for 3 hours and 15 minutes. The reaction was filtered using ethyl acetate and the solvent was evaporated under reduced pressure. The crude product was purified by column chromatography on silica gel (0-100% ethyl acetate in hexane) to yield 1-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)-N-(6-(1-(2-hydroxyethyl)-5-methyl-2-oxo-1,2-dihydropyridin-3-yl)-5-methylpyridin-2-yl)cyclopropanecarboxamide as a white solid (5.5 g, 33.6%). ESI-MS m/z calc. 483.46. found 484.5 (M+1)+, retention time 1.49 minutes

Workup

filtrationThe reaction was filtered
customthe solvent was evaporated under reduced pressure
customThe crude product was purified by column chromatography on silica gel (0-100% ethyl acetate in hexane)

Sources & evidence

ORD record: ord-a66cd1a53462446bb8169b80a97e295b
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08969386B2

Reaction notes

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