Water → HCID 178523020, compound

HRID 2244224Notes

Reaction equation

[C:1]([CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[CH:15]=[CH:14][C:13]([C:16]([N:18]2[C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=3[CH2:22][N:21]3[C:29]([C:32]([NH:34][CH2:35][C:36]4[CH:37]=[N:38][CH:39]=[CH:40][CH:41]=4)=[O:33])=[CH:30][CH:31]=[C:20]3[CH2:19]2)=[O:17])=[CH:12][CH:11]=1)#[N:2].[N-:42]=[N+:43]=[N-:44].[Na+].[Cl-].[NH4+].O>CS(C)=O>[N:38]1[CH:39]=[CH:40][CH:41]=[C:36]([CH2:35][NH:34][C:32]([C:29]2[N:21]3[C:20]([CH2:19][N:18]([C:16]([C:13]4[CH:12]=[CH:11][C:10]([C:5]5[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=5[CH2:3][C:1]5[NH:44][N:43]=[N:42][N:2]=5)=[CH:15][CH:14]=4)=[O:17])[C:24]4[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=4[CH2:22]3)=[CH:31][CH:30]=2)=[O:33])[CH:37]=1

Participants

Conditions

Temperature: 50 °C

Procedure

A mixture of 0.537 g (0.001 mol) of 10-{[2′-(cyanomethyl)-1,1′-biphenyl-4-yl]carbonyl}-N-(pyridin-3-ylmethyl)-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine-3-carboxamide of Example 17, 0.32 g (0.005 mole) of sodium azide and 0.26 g (0.005 mole) of ammonium chloride in 20 mL of dimethyl sulfoxide was heated with stirring at 50° C. for three hours. The reaction mixure was poured into 100 mL of water, and the precipitated crude product was subjected to chromatographic purification giving 0.46 g of title compound, m.p. 164-167° C.

Workup

temperaturewas heated
customthe precipitated crude product
customwas subjected to chromatographic purification

Sources & evidence

ORD record: ord-df9b8dd357c94d84bfd75d29e59cd26e
Source dataset: uspto-grants-2010_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07678787B2

Reaction notes

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