Lithium Hydroxide → HCID 71559324, compound

HRID 1024031Notes

Reaction equation

HRID 1024031 reaction equation
C([O:4][CH2:5][C:6]1[C:11]([N:12]2[CH2:24][CH2:23][N:15]3[C:16]4[CH2:17][CH2:18][CH2:19][CH2:20][C:21]=4[CH:22]=[C:14]3[C:13]2=[O:25])=[CH:10][C:9]([F:26])=[CH:8][C:7]=1[C:27]1[N:28]=[C:29]([NH:36][C:37]2[CH:42]=[CH:41][C:40]([N:43]3[CH2:48][CH2:47][N:46]([CH3:49])[CH2:45][CH2:44]3)=[CH:39][N:38]=2)[C:30]2[N:31]([CH:33]=[CH:34][N:35]=2)[CH:32]=1)(=O)C.[Li+].[OH-]>CC(O)C.C1COCC1.O>[F:26][C:9]1[CH:8]=[C:7]([C:27]2[N:28]=[C:29]([NH:36][C:37]3[CH:42]=[CH:41][C:40]([N:43]4[CH2:44][CH2:45][N:46]([CH3:49])[CH2:47][CH2:48]4)=[CH:39][N:38]=3)[C:30]3[N:31]([CH:33]=[CH:34][N:35]=3)[CH:32]=2)[C:6]([CH2:5][OH:4])=[C:11]([N:12]2[CH2:24][CH2:23][N:15]3[C:16]4[CH2:17][CH2:18][CH2:19][CH2:20][C:21]=4[CH:22]=[C:14]3[C:13]2=[O:25])[CH:10]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 86684129HCID 86684129, compound

Product 1

HCID 71559324HCID 71559324, compoundYield 20%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 22597222Tetrahydrofuran 2-propanolSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 106d (200 mg, 0.92 mmol) and LiOH (300 mg, 10 mmol) in iPrOH/THF (1:1, 3.5 mL) and H2O (1 mL) was stirred at 50° C. for 0.5 h. The mixture was evaporated in vacuo and the residue was extracted with Ethyl acetate (10 mL×2). The combined Ethyl acetate extract was concentrated under reduced pressure and the residue was purified with reverse-phase prep-HPLC to afford 106 (45 mg, 20%). LCMS: [M+H]+ 622. 1H NMR (500 MHz, DMSO) δ 9.04 (s, 1H), 8.41 (s, 1H), 8.13-8.10 (m, 2H), 7.98 (s, 1H), 7.71 (s, 1H), 7.47-7.44 (m, 2H), 7.39-7.37 (m, 1H), 6.53 (s, 1H), 5.38-5.36 (m, 1H), 4.37-4.44 (m, 2H), 4.19-3.98 (m, 4H), 3.12 (s, 4H), 2.60-2.58 (m, 2H), 2.50-2.45 (m, 6H), 2.21 (s, 3H), 1.79-1.68 (m, 2H), 1.69-1.67 (m, 2H)

Workup

  1. customThe mixture was evaporated in vacuo
  2. extractionthe residue was extracted with Ethyl acetate (10 mL×2)
  3. extractionThe combined Ethyl acetate extract
  4. concentrationwas concentrated under reduced pressure
  5. customthe residue was purified with reverse-phase prep-HPLC

Sources & evidence

ORD record
ord-e9e02f630eb74108b1cf08ef17da8dbf
Source dataset
uspto-grants-2014_05
Patent number
US08722676B2

Reaction notes

Loading…