Water → 5-[4-[(2-Chloropyridin-3-yl)carbonylamino]phenyl]-8,9,10,11-tetrahydro-1H-[1,4]diazepino[2,3-f]isoquinoline-2,4(3H,5H)-dione

HRID 1049835Notes

Reaction equation

HRID 1049835 reaction equation
[Cl:1][C:2]1[C:7]([C:8]([NH:10][C:11]2[CH:16]=[CH:15][C:14]([N:17]3[C:31]4[C:22](=[C:23]5[C:28](=[CH:29][CH:30]=4)[CH:27]=[N:26][CH:25]=[CH:24]5)[NH:21][C:20](=[O:32])[CH2:19][C:18]3=[O:33])=[CH:13][CH:12]=2)=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1.[BH4-].[Na+].O.C(=O)([O-])[O-].[Na+].[Na+]>C(O)(=O)C>[Cl:1][C:2]1[C:7]([C:8]([NH:10][C:11]2[CH:12]=[CH:13][C:14]([N:17]3[C:31]4[C:22](=[C:23]5[C:28](=[CH:29][CH:30]=4)[CH2:27][NH:26][CH2:25][CH2:24]5)[NH:21][C:20](=[O:32])[CH2:19][C:18]3=[O:33])=[CH:15][CH:16]=2)=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 4311764Sodium borohydride2×HCID 716572715-[4-[(2-Chloropyridin-3-yl)carbonylamino]phenyl]-1H-[1,4]diazepino[2,3-f]isoquinoline-2,4(3H,5H)-dione

Product 1

HCID 716573735-[4-[(2-Chloropyridin-3-yl)carbonylamino]phenyl]-8,9,10,11-tetrahydro-1H-[1,4]diazepino[2,3-f]isoquinoline-2,4(3H,5H)-dioneYield 68.9%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

5-[4-[(2-Chloropyridin-3-yl)carbonylamino]phenyl]-1H-[1,4]diazepino[2,3-f]isoquinoline-2,4(3H,5H)-dione (10 mg, 0.022 mmol) was dissolved in acetic acid (0.4 mL), the solution was added with sodium borohydride (64 mg, 0.11 mmol), the mixture was stirred at room temperature for 2 hours, and then further added with sodium borohydride (64 mg, 0.11 mmol), and the mixture was stirred at room temperature for 2 hours. This reaction mixture was added with water, made basic with sodium carbonate, and extracted three times with chloroform, and the organic layer was dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was washed with ethyl acetate to give the title compound (7 mg, yield 68%) as pale brown crystals.

Workup

  1. stirringthe mixture was stirred at room temperature for 2 hours
  2. extractionextracted three times with chloroform
  3. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. washthe residue was washed with ethyl acetate

Sources & evidence

ORD record
ord-827c4c5228954828a3ac8211772f42de
Source dataset
uspto-grants-2016_07
Patent number
US09382236B2

Reaction notes

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