Lithium Hydroxide → HCID 71553394, compound

HRID 1430232Notes

Reaction equation

HRID 1430232 reaction equation
[CH:1]([N:14]1[CH:18]=[C:17]([C:19]2[C:20]([C:47]([O:49]C(C)(C)C)=[O:48])=[N:21][C:22]([N:25]3[CH2:34][CH2:33][C:32]4[C:27](=[C:28]([C:35](=[O:46])[NH:36][C:37]5[S:38][C:39]6[CH:45]=[CH:44][CH:43]=[CH:42][C:40]=6[N:41]=5)[CH:29]=[CH:30][CH:31]=4)[CH2:26]3)=[CH:23][CH:24]=2)[CH:16]=[N:15]1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Li+]>O1CCCC1.CO>[S:38]1[C:39]2[CH:45]=[CH:44][CH:43]=[CH:42][C:40]=2[N:41]=[C:37]1[NH:36][C:35]([C:28]1[CH:29]=[CH:30][CH:31]=[C:32]2[C:27]=1[CH2:26][N:25]([C:22]1[N:21]=[C:20]([C:47]([OH:49])=[O:48])[C:19]([C:17]3[CH:16]=[N:15][N:14]([CH:1]([C:8]4[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=4)[C:2]4[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=4)[CH:18]=3)=[CH:24][CH:23]=1)[CH2:34][CH2:33]2)=[O:46]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 89498454HCID 89498454, compound

Product 1

HCID 71553394HCID 71553394, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A suspension of EXAMPLE 75B (30 mg) and lithium hydroxide (2 mg) in tetrahydrofuran and methanol (2:1, 1 mL) was heated at 60° C. for 16 hours. The reaction mixture was quenched with HCl (0.2 mL, 1M), concentrated and purified by chromatography on silica gel using 0-5% methanol/dichloromethane as eluent to provide the title compound. 1H NMR (300 MHz, dimethylsulfoxide-d6) δ ppm 13.14 (s, 1H), 12.87 (s, 1H), 8.04 (d, 1H), 7.82 (s, 1H), 7.79 (d, 1H), 7.73 (d, 1H), 7.66 (s, 1H), 7.61 (d, 1H), 7.44-7.51 (m, 1H), 7.40-7.44 (m, 1H), 7.29-7.40 (m, 5H), 7.19 (d, 4H), 6.93 (t, 2H), 4.94 (s, 2H), 3.94 (s, 1H), 3.86 (t, 2H), 2.99 (t, 1H).

Workup

  1. customThe reaction mixture was quenched with HCl (0.2 mL, 1M)
  2. concentrationconcentrated
  3. custompurified by chromatography on silica gel using 0-5% methanol/dichloromethane as eluent

Sources & evidence

ORD record
ord-9751d57160b14c7d8141b185a81af540
Source dataset
uspto-grants-2015_01
Patent number
US08940737B2

Reaction notes

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