Trifluoroacetic acid → 3-(4-Oxo-7-pyridin-4-yl-4,5-dihydro-3H-benzo[b][1,4]diazepin-2-yl)-benzonitrile

HRID 1745694Notes

Reaction equation

HRID 1745694 reaction equation
C(OC(=O)[NH:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=2)=[CH:10][C:9]=1[NH2:20])(C)(C)C.CC1(C)O[C:27]([C:29]2[CH:30]=[C:31]([CH:34]=[CH:35][CH:36]=2)[C:32]#[N:33])=[CH:26][C:25](=[O:37])O1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[O:37]=[C:25]1[CH2:26][C:27]([C:29]2[CH:30]=[C:31]([CH:34]=[CH:35][CH:36]=2)[C:32]#[N:33])=[N:7][C:8]2[CH:13]=[CH:12][C:11]([C:14]3[CH:15]=[CH:16][N:17]=[CH:18][CH:19]=3)=[CH:10][C:9]=2[NH:20]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 117363373-(2,2-Dimethyl-6-oxo-6H-[1,3]dioxin-4-yl)-benzonitrileHCID 59737204Tert-butyl 2-amino-4-(pyridin-4-yl)phenylcarbamate

Product 1

HCID 222249143-(4-Oxo-7-pyridin-4-yl-4,5-dihydro-3H-benzo[b][1,4]diazepin-2-yl)-benzonitrile

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Prepared from (2-amino-4-pyridin-4-yl-phenyl)-carbamic acid tert.-butyl ester (Example G28) and 3-(2,2-dimethyl-6-oxo-6H-[1,3]dioxin-4-yl)-benzonitrile (Example J4) according to the general procedure K. The obtained material was deprotected and cyclized by treatment with TFA in CH2Cl2 according to the general procedure M. Obtained as a red-brown solid (25 mg).

Sources & evidence

ORD record
ord-51981fe9622e48ea8dc7144b854a33cd
Source dataset
uspto-grants-2006_03
Patent number
US07018998B2

Reaction notes

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