Sodium borohydride → HCID 71556958, compound

HRID 1021733Notes

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][C:33]4[C:32]5[CH2:31][C:30]([CH3:37])([CH3:36])[CH2:29][C:28]=5[S:27][C:26]=4[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][C:33]3[C:32]4[CH2:31][C:30]([CH3:36])([CH3:37])[CH2:29][C:28]=4[S: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 143b (110 mg, 0.2 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 afford 143 (48 mg, 44%). LCMS: [M+H]+ 529. 1H NMR (500 MHz, DMSO) δ 9.23 (s, 1H), 8.76 (d, J=2.5, 1H), 8.65 (s, 1H), 8.51-8.49 (m, 1H), 8.31 (m, 1H), 7.67 (d, J=3.0, 1H), 7.38-7.37 (m, 1H), 7.33-7.31 (m, 1H), 5.02-5.01 (m, 1H), 4.43 (d, J=2.5, 2H), 4.18-4.15 (m, 1H), 3.83-3.81 (m, 1H), 3.61-3.59 (m, 3H), 3.03-2.99 (m, 1H), 2.91-2.89 (m, 1H), 2.76 (s, 2H), 2.60-2.53 (m, 2H), 1.23-1.22 (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-b45e54e0c07747c3a0a1d13b62f609a7
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08716274B2

Reaction notes

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