Water → HCID 117699168, compound

HRID 1049803Notes

Reaction equation

HRID 1049803 reaction equation
Cl[C:2]1[CH:30]=[CH:29][C:5]2[N:6]([C:13]3[CH:18]=[CH:17][C:16]([NH:19][S:20]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)(=[O:22])=[O:21])=[CH:15][CH:14]=3)[C:7](=[O:12])[CH2:8][C:9](=[O:11])[NH:10][C:4]=2[CH:3]=1.O1CCCC1.O.C([O-])=O.[NH4+]>CO>[O:12]=[C:7]1[N:6]([C:13]2[CH:14]=[CH:15][C:16]([NH:19][S:20]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)(=[O:22])=[O:21])=[CH:17][CH:18]=2)[C:5]2[CH:29]=[CH:30][CH:2]=[CH:3][C:4]=2[NH:10][C:9](=[O:11])[CH2:8]1

Participants

6

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 2723923Ammonium formateHCID 117699089HCID 117699089, compound

Product 1

HCID 117699168HCID 117699168, compoundYield 77.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

N-[4-(7-Chloro-2,4-dioxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-1-yl)phenyl]benzenesulfonamide (28 mg, 0.06 mmol) obtained in Example 169 was dissolved in methanol (0.6 mL), tetrahydrofuran (0.6 mL), and water (0.6 mL), the solution was added with ammonium formate (38 mg, 0.6 mmol), and the mixture was stirred at room temperature for 16 hours. After completion of the reaction, the reaction mixture was filtered through Cerite, and the solvent was evaporated under reduced pressure. The obtained residue was added with water, the mixture was extracted with chloroform, and the organic layer was dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (chloroform/methanol=100/1) to obtain the title compound (19 mg, yield 77%).

Workup

  1. customAfter completion of the reaction
  2. filtrationthe reaction mixture was filtered through Cerite
  3. customthe solvent was evaporated under reduced pressure
  4. additionThe obtained residue was added with water
  5. extractionthe mixture was extracted with chloroform
  6. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  7. customThe solvent was evaporated under reduced pressure
  8. customthe residue was purified by silica gel column chromatography (chloroform/methanol=100/1)

Sources & evidence

ORD record
ord-8123d2502a234196a7d41e00e45d9087
Source dataset
uspto-grants-2016_07
Patent number
US09382236B2

Reaction notes

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