Ammonium Hydroxide → HCID 10200034, compound

HRID 1635884Notes

Reaction equation

C[O:2][C:3]1[CH:8]=[C:7]([N:9]2[CH:13]=[CH:12][C:11]([CH3:14])=[N:10]2)[CH:6]=[CH:5][C:4]=1[C:15]([N:17]1[C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=2[CH2:21][N:20]2[CH:28]=[CH:29][CH:30]=[C:19]2[CH2:18]1)=[O:16].B(Br)(Br)Br.[OH-].[NH4+]>ClCCl>[OH:2][C:3]1[CH:8]=[C:7]([N:9]2[CH:13]=[CH:12][C:11]([CH3:14])=[N:10]2)[CH:6]=[CH:5][C:4]=1[C:15]([N:17]1[C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=2[CH2:21][N:20]2[CH:28]=[CH:29][CH:30]=[C:19]2[CH2:18]1)=[O:16]

Participants

Conditions

Temperature: -78 °C

Procedure

[2-Methoxy-4-(3-methyl-pyrazol-1-yl)-phenyl](5H,11H-pyrrolo[2,1-c][1,4]-benzodiazepin-10-yl) methanone (0.82 g) from Example 107 was dissolved in dichloromethane (20 ml) and cooled to −78° C. Boron tribromide (6.2 ml) was added and the reaction stirred at 0° C. for five minutes. Ammonium hydroxide (15 ml) was added and extracted with dichloromethane. The organic phase was washed with brine and dried over anhydrous magnesium sulfate. The solid was removed by filtration and the solvent removed in vacuo. The residue was purified by flash column chromatography on silica pressure eluting with hexane/ethyl acetate (3/1 then 2/1) to afford 0.19 g of the title compound as a colorless solid, m.p. 134-136° C.

Workup

extractionextracted with dichloromethane
washThe organic phase was washed with brine
dry with materialdried over anhydrous magnesium sulfate
customThe solid was removed by filtration
customthe solvent removed in vacuo
customThe residue was purified by flash column chromatography on silica pressure
washeluting with hexane/ethyl acetate (3/1

Sources & evidence

ORD record: ord-77a4fcd287e3471091f23d65fee15711
Source dataset: uspto-grants-2003_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06511974B1

Reaction notes

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