Hydrogen Peroxide → HCID 42636084, compound

HRID 1971028Notes

Reaction equation

HRID 1971028 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[C:9](B3OC(C)(C)C(C)(C)O3)=[CH:10][C:11]3[C:12]4[C:20]([NH:21][C@H:22]([CH:27]5[CH2:29][CH2:28]5)[C:23]([F:26])([F:25])[F:24])=[N:19][CH:18]=[C:17]([C:30]([NH2:32])=[O:31])[C:13]=4[NH:14][C:15]=3[CH:16]=2)=[CH:4][N:3]=1.[OH:42]O>CC(O)=O.CCOC(C)=O>[NH2:1][C:2]1[N:3]=[CH:4][C:5]([C:8]2[C:9]([OH:42])=[CH:10][C:11]3[C:12]4[C:20]([NH:21][C@H:22]([CH:27]5[CH2:28][CH2:29]5)[C:23]([F:26])([F:24])[F:25])=[N:19][CH:18]=[C:17]([C:30]([NH2:32])=[O:31])[C:13]=4[NH:14][C:15]=3[CH:16]=2)=[CH:6][N:7]=1

Participants

5

Reactant 2

HCID 784Hydrogen PeroxideHCID 59543153HCID 59543153, compound

Product 1

HCID 42636084HCID 42636084, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 7-(2-aminopyrimidin-5-yl)-{[(1R)-1-cyclopropyl-2,2,2-trifluoroethyl]amino}-8-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5H-pyrido[4,3-b]indole-4-carboxamide (218 mg, 0.38 mmol) in AcOH (7.7 mL) was added hydrogen peroxide (30%, 0.20 mL, 1.9 mmol) at 0° C. The reaction was left to stir at room temperature for 3 h, diluted with EtOAc, and washed with water. The organic layer was dried, concentrated, and purified by flash chromatography to afford the title compound. 1H NMR (500 MHz, CD3SOCD3) δ 11.38 (s, 1H); 9.25 (s, 1H); 8.42 (s, 2H); 7.97 (s, 1H); 7.90 (br s, 1H); 7.75 (s, 1H); 7.60 (s, 1H); 7.22 (br s, 1H); 6.63 (m, 2H); 4.86 (m, 1H); 1.45 (m, 1H); 0.72 (m, 1H); 0.60 (m, 1H); 0.53 (m, 1H); 0.36 (m, 1H). LRMS (APCI) calc'd for (C21H18F3N7O2) [M+H]+, 458.1. found 458.1.

Workup

  1. waitThe reaction was left
  2. washwashed with water
  3. customThe organic layer was dried
  4. concentrationconcentrated
  5. custompurified by flash chromatography

Sources & evidence

ORD record
ord-2718f8f221ff48fd92653c11ff7912cb
Source dataset
uspto-grants-2013_04
Patent number
US08431569B2

Reaction notes

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