Sodium borohydride → HCID 71556957, compound

HRID 1411599Notes

Reaction equation

[BH4-].[Na+].[F:3][C:4]1([F:52])[CH2:12][C:11]2[N:10]3[CH2:13][CH2:14][N:15]([C:18]4[N:25]=[CH:24][CH:23]=[C:22]([C:26]5[CH:31]=[C:30]([NH:32][C:33]6[CH:38]=[CH:37][C:36]([N:39]7[CH2:44][CH2:43][N:42]([CH:45]8[CH2:48][O:47][CH2:46]8)[CH2:41][C@@H:40]7[CH3:49])=[CH:35][N:34]=6)[C:29](=[O:50])[N:28]([CH3:51])[CH:27]=5)[C:19]=4[CH:20]=[O:21])[C:16](=[O:17])[C:9]3=[CH:8][C:7]=2[CH2:6][CH2:5]1>>[F:52][C:4]1([F:3])[CH2:12][C:11]2[N:10]3[CH2:13][CH2:14][N:15]([C:18]4[C:19]([CH2:20][OH:21])=[C:22]([C:26]5[CH:31]=[C:30]([NH:32][C:33]6[CH:38]=[CH:37][C:36]([N:39]7[CH2:44][CH2:43][N:42]([CH:45]8[CH2:48][O:47][CH2:46]8)[CH2:41][C@@H:40]7[CH3:49])=[CH:35][N:34]=6)[C:29](=[O:50])[N:28]([CH3:51])[CH:27]=5)[CH:23]=[CH:24][N:25]=4)[C:16](=[O:17])[C:9]3=[CH:8][C:7]=2[CH2:6][CH2:5]1

Participants

Reactant 2

HCID 4311764Sodium borohydride

HCID 86684249HCID 86684249, compound

Product 1

HCID 71556957HCID 71556957, compoundYield 51.8%

Procedure

Following the procedures as described in Example 130, sodium borohydride reduction of 140a (200 mg) afforded 140 as a yellow solid (104 mg, 51%). LCMS: [M+H]+ 686.3. 1H NMR (500 MHz, DMSO) δ 8.62 (d, J=2.0, 1H), 8.46-8.49 (m, 2H), 7.83 (d, J=3.0, 1H), 7.45 (d, J=2.5, 1H), 7.35-7.38 (m, 2H), 7.25 (d, J=9.5, 1H), 6.64 (s, 1H), 4.95-4.97 (m, 1H), 4.54-4.57 (m, 2H), 4.38-4.48 (m, 4H), 4.15-4.27 (m, 3H), 3.87-3.90 (m, 1H), 3.67 (s, 1H), 3.59 (s, 3H), 3.26-3.39 (m, 3H), 3.08-3.10 (m, 1H), 2.92-2.96 (m, 1H), 2.63-2.67 (m, 2H), 2.52-2.55 (m, 1H), 2.30-2.36 (m, 2H), 2.18-2.24 (m, 3H), 0.93 (d, J=6.0, 3H)

Sources & evidence

ORD record: ord-2b9067359dfa44b48d2822c7ea707b33
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08921353B2

Reaction notes

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