Sodium cyanoborohydride → HCID 67226839, compound

HRID 1520596Notes

Reaction equation

HRID 1520596 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[CH2:14][N:15]2[CH2:20][CH2:19][N:18]([C:21]3[CH:49]=[CH:48][C:24]([C:25]([NH:27][S:28]([C:31]4[CH:36]=[CH:35][C:34]([NH:37][CH2:38][CH:39]5[CH2:44][CH2:43][O:42][CH2:41][CH2:40]5)=[C:33]([N+:45]([O-:47])=[O:46])[CH:32]=4)(=[O:30])=[O:29])=[O:26])=[C:23]([O:50][C:51]4[CH:52]=[C:53]5[C:57](=[CH:58][CH:59]=4)[NH:56][CH:55]=[CH:54]5)[CH:22]=3)[CH2:17][CH2:16]2)=[CH:4][CH:3]=1.C([BH3-])#N.[Na+]>C(O)(=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[CH2:14][N:15]2[CH2:16][CH2:17][N:18]([C:21]3[CH:49]=[CH:48][C:24]([C:25]([NH:27][S:28]([C:31]4[CH:36]=[CH:35][C:34]([NH:37][CH2:38][CH:39]5[CH2:44][CH2:43][O:42][CH2:41][CH2:40]5)=[C:33]([N+:45]([O-:47])=[O:46])[CH:32]=4)(=[O:30])=[O:29])=[O:26])=[C:23]([O:50][C:51]4[CH:52]=[C:53]5[C:57](=[CH:58][CH:59]=4)[NH:56][CH2:55][CH2:54]5)[CH:22]=3)[CH2:19][CH2:20]2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 5003444Sodium cyanoborohydrideHCID 46834430HCID 46834430, compound

Product 1

HCID 67226839HCID 67226839, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A suspension of EXAMPLE 40D (22.57 mg) and sodium cyanoborohydride (25 mg) in acetic acid (5 ml) was stirred at room temperature for 2 hours. The product was partitioned between dichloromethane and water. The organic layer was separated, dried over Na2SO4, and concentrated. The crude product was purified by RP HPLC (C8, 30-100 acetonitrile/water/0.1% trifluoroacetic acid). 1H NMR (300 MHz, dimethylsulfoxide-d6) δ 11.56 (s, 1H), 9.60 (s, 1H), 8.66 (t, 1H), 8.57 (d, 1H), 7.85 (dd, 1H), 7.71 (s, 1H), 7.46-7.60 (m, 5H), 7.29-7.42 (m, 3H), 7.25 (d, 1H), 6.95 (s, 1H), 6.82 (s, 1H), 6.73 (d, 1H), 6.36 (s, 1H), 4.32 (bs, 2H), 3.85 (dd, 4H), 3.59 (t, 4H), 3.35 (t, 2H), 3.27 (t, 2H), 3.02 (t, 4H), 1.80-1.99 (m, 1H), 1.62 (d, 2H), 1.15-1.36 (m, 2H).

Workup

  1. customThe product was partitioned between dichloromethane and water
  2. customThe organic layer was separated
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customThe crude product was purified by RP HPLC (C8, 30-100 acetonitrile/water/0.1% trifluoroacetic acid)

Sources & evidence

ORD record
ord-f36d17e9c2ef4546acd25517cf696064
Source dataset
uspto-grants-2015_07
Patent number
US09073855B2

Reaction notes

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