Ammonia → HCID 117699275, compound

HRID 1049690Notes

Reaction equation

HRID 1049690 reaction equation
C[O:2][C:3]1[CH:34]=[CH:33][CH:32]=[CH:31][C:4]=1[C:5]([NH:7][C:8]1[CH:13]=[CH:12][C:11]([N:14]2[C:20](=[O:21])[CH2:19][C:18](=[O:22])[NH:17][C:16]3[C:23]4[C:28]([CH:29]=[CH:30][C:15]2=3)=[CH:27][CH:26]=[CH:25][CH:24]=4)=[CH:10][CH:9]=1)=[O:6].B(Br)(Br)Br.N>ClCCl>[OH:2][C:3]1[CH:34]=[CH:33][CH:32]=[CH:31][C:4]=1[C:5]([NH:7][C:8]1[CH:9]=[CH:10][C:11]([N:14]2[C:20](=[O:21])[CH2:19][C:18](=[O:22])[NH:17][C:16]3[C:23]4[C:28]([CH:29]=[CH:30][C:15]2=3)=[CH:27][CH:26]=[CH:25][CH:24]=4)=[CH:12][CH:13]=1)=[O:6]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 25134Boron tribromideHCID 117699092HCID 117699092, compound

Product 1

HCID 117699275HCID 117699275, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

5-[4-(2-Methoxybenzoylamino)phenyl]-1H-naphtho[1,2-b][1,4]diazepine-2,4(3H,5H)-dione (56 mg, 0.124 mmol) obtained in Example 12 was dissolved in dichloromethane (1.2 mL), the solution was added with a 1 M solution of boron tribromide in dichloromethane (0.37 mL, 0.37 mmol) on an ice bath, and the mixture was stirred at room temperature for 16 hours. After completion of the reaction, the reaction mixture was added with 25% aqueous ammonia, and the mixture was extracted with chloroform. Then, the organic layer was dried over sodium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (chloroform/methanol=100/1) to give the title compound (39 mg, yield 72%).

Workup

  1. customAfter completion of the reaction
  2. extractionthe mixture was extracted with chloroform
  3. dry with materialThen, the organic layer was dried over sodium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (chloroform/methanol=100/1)

Sources & evidence

ORD record
ord-fb85377e08e045c48daea9123441b169
Source dataset
uspto-grants-2016_07
Patent number
US09382236B2

Reaction notes

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