Sodium borohydride → HCID 86567258, compound

HRID 1411607Notes

Reaction equation

[CH3:1][N:2]1[C:7](=[O:8])[C:6]([NH:9][C:10]2[CH:15]=[CH:14][N:13]=[CH:12][N:11]=2)=[CH:5][C:4]([C:16]2[C:21]([CH:22]=[O:23])=[C:20]([N:24]3[CH2:35][CH2:34][N:33]4[C:26](=[CH:27][C:28]5[CH2:29][C:30]([CH3:37])([CH3:36])[CH2:31][C:32]=54)[C:25]3=[O:38])[N:19]=[CH:18][CH:17]=2)=[CH:3]1.[BH4-].[Na+]>CO>[OH:23][CH2:22][C:21]1[C:20]([N:24]2[CH2:35][CH2:34][N:33]3[C:32]4[CH2:31][C:30]([CH3:36])([CH3:37])[CH2:29][C:28]=4[CH:27]=[C:26]3[C:25]2=[O:38])=[N:19][CH:18]=[CH:17][C:16]=1[C:4]1[CH:5]=[C:6]([NH:9][C:10]2[CH:15]=[CH:14][N:13]=[CH:12][N:11]=2)[C:7](=[O:8])[N:2]([CH3:1])[CH:3]=1

Participants

Conditions

Temperature: 25 °C

Procedure

A mixture of 144a (98 mg, 0.19 mmol), NaBH4 (30 mg, 0.8 mmol) and MeOH (5 mL) was stirred at 25° C. for 30 mins. The mixture was evaporated in vacuo and the residue was extracted with EtOAc (10 mL×2). The combined EtOAc extract was concentrated under reduced pressure and the residue was purified with reverse-phase prep-HPLC to give 144 (25 mg, 42%). LCMS: [M+H]+ 512. 1H NMR (500 MHz, DMSO) δ 9.18 (s, 1H), 8.76-8.74 (m, 1H), 8.64 (s, 1H), 8.50-8.47 (m, 1H), 8.31-8.30 (m, 1H), 7.68-7.69 (m, 1H), 7.37-7.36 (m, 1H), 7.33-7.31 (m, 1H), 6.56 (s, 1H), 5.07-5.04 (m, 1H), 4.44-4.41 (m, 2H), 4.23-4.18 (m, 3H), 3.86-3.84 (m, 1H), 3.61 (s, 3H), 2.61-2.56 (m, 2H), 2.42 (s, 2H), 1.21-1.20 (m, 6H)

Workup

customThe mixture was evaporated in vacuo
extractionthe residue was extracted with EtOAc (10 mL×2)
extractionThe combined EtOAc extract
concentrationwas concentrated under reduced pressure
customthe residue was purified with reverse-phase prep-HPLC

Sources & evidence

ORD record: ord-c06e25c1d8a2431ca1917bf559919f2b
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08921353B2

Reaction notes

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