Trifluoroacetic acid → (S)-3-Amino-5-phenyl-1-(5-chloropyridin-2-yl)-1H-benzo[e][1,4]diazepin-2(3H)-one

HRID 2276872Notes

Reaction equation

HRID 2276872 reaction equation
[O:1]=[C:2]1[NH:8][C:7]2[CH:9]=[CH:10][CH:11]=[CH:12][C:6]=2[C:5]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[N:4][CH:3]1[NH:19]C(=O)OCC1C=CC=CC=1.[Cl:30][C:31]1[CH:32]=[CH:33][C:34](I)=[N:35][CH:36]=1.C(O)(C(F)(F)F)=O>O.CO>[NH2:19][C@@H:3]1[C:2](=[O:1])[N:8]([C:34]2[CH:33]=[CH:32][C:31]([Cl:30])=[CH:36][N:35]=2)[C:7]2[CH:9]=[CH:10][CH:11]=[CH:12][C:6]=2[C:5]([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)=[N:4]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 2756242Benzyl (2-oxo-5-phenyl-2,3-dihydro-1h-benzo[e][1,4]diazepin-3-yl)carbamateHCID 111181485-Chloro-2-iodopyridine

Product 1

HCID 90080293(S)-3-Amino-5-phenyl-1-(5-chloropyridin-2-yl)-1H-benzo[e][1,4]diazepin-2(3H)-one

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

Intermediate B-16 was prepared from benzyl 2-oxo-5-phenyl-2,3-dihydro-1H-benzo[e][1,4]diazepin-3-ylcarbamate and 5-chloro-2-iodopyridine according to the procedure described for Intermediate B-15. RT=2.430 min (H2O/CH3OH with TFA, CHROMOLITH® ODS S5 4.6×50 mm, gradient=3 min, wavelength=220 and 254 nm); MS(ES):m/z=363.12 [M+H+].

Sources & evidence

ORD record
ord-cc96c08f77794b75a1087ac1505ad827
Source dataset
uspto-grants-2015_09
Patent number
US09133139B2

Reaction notes

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