Hydrogen Peroxide → HCID 86343291, compound

HRID 1504104Notes

Reaction equation

HRID 1504104 reaction equation
[N:1]1([CH:7]2[CH2:12][CH2:11][CH:10]([NH:13][C:14]3[N:15]=[CH:16][N:17]=[C:18]4[C:25]=3[C:24]3[C@@H:23]([CH2:26][C:27]#[N:28])[CH2:22][CH2:21][C:20]=3[S:19]4)[CH2:9][CH2:8]2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[OH:29]O>CO.C(Cl)Cl>[N:1]1([CH:7]2[CH2:8][CH2:9][CH:10]([NH:13][C:14]3[N:15]=[CH:16][N:17]=[C:18]4[C:25]=3[C:24]3[C@@H:23]([CH2:26][C:27]([NH2:28])=[O:29])[CH2:22][CH2:21][C:20]=3[S:19]4)[CH2:11][CH2:12]2)[CH2:2][CH2:3][O:4][CH2:5][CH2:6]1

Participants

5

Reactant 2

HCID 784Hydrogen PeroxideHCID 89693945HCID 89693945, compound

Product 1

HCID 86343291HCID 86343291, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-[(3R)-12-[[4-(morpholin-4-yl)cyclohexyl]amino]-7-thia-9,11-diazatricyclo[6.4.0.0^[2,6]]dodeca-1(12),2(6),8,10-tetraen-3-yl]acetonitrile (120 mg, 0.30 mmol, 1.00 equiv) in methanol (8 mL) was added LiOR.H2O (37.8 mg, 0.90 mmol, 3.00 equiv) and H2O2 (30%, 0.5 mL) in an ice-water bath. The resulting solution was stirred for 2 h at room temperature and diluted with DCM (30 mL), washed with brine, dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column with DCM/MeOH (20:1) to give 100 mg (80%) of 2-[(3R)-12-[[4-(morpholin-4-yl)cyclohexyl]amino]-7-thia-9,11-diazatricyclo[6.4.0.0^[2,6]]dodeca-1(12),2(6),8,10-tetraen-3-yl]acetamide as a white solid. MS (ES): m/z 416 (M+H)+. 1H NMR (400 MHz, CD3OD): δ 8.23 (s, 1H), 4.11-4.20 (m, 1H), 3.82-3.89 (m, 1H), 3.72 (s, 4H), 3.09-3.17 (m, 1H), 2.93-2.99 (m, 1H), 2.70-2.82 (m, 1H), 2.65 (s, 4H), 2.47 (s, 2H), 2.27-2.35 (m, 2H), 2.11-2.19 (m, 2H), 2.05-2.10 (m, 2H), 1.40-1.67 (m, 4H).

Workup

  1. washwashed with brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-368dfb2222d044238590d19badc71c11
Source dataset
uspto-grants-2015_12
Patent number
US09212190B2

Reaction notes

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