Triphenylphosphine → 3-Amino-7-fluoro-1,3-dihydro-1-methyl-5-phenyl-2H-1,4-benzodiazepin-2-one

HRID 2223090Notes

Reaction equation

HRID 2223090 reaction equation
[N:1]([CH:4]1[N:10]=[C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:8]2[CH:17]=[C:18]([F:21])[CH:19]=[CH:20][C:7]=2[N:6]([CH3:22])[C:5]1=[O:23])=[N+]=[N-].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>>[NH2:1][CH:4]1[N:10]=[C:9]([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:8]2[CH:17]=[C:18]([F:21])[CH:19]=[CH:20][C:7]=2[N:6]([CH3:22])[C:5]1=[O:23]

Participants

3

Reactant 2

HCID 11776TriphenylphosphineHCID 597138183-azido-7-fluoro-1,3-dihydro-1-methyl-5-phenyl-2H-1,4-benzodiazepin-2-one

Product 1

HCID 597144553-Amino-7-fluoro-1,3-dihydro-1-methyl-5-phenyl-2H-1,4-benzodiazepin-2-one

Procedure

As illustrated in the scheme above and following General Procedure 7, 3-azido-7-fluoro-1,3-dihydro-1-methyl-5-phenyl-2H-1,4-benzodiazepin-2-one (0.0826 g, 0.267 mmol) and PS—PPh3 (1.63 g of 1.64 mmol/g, 2.67 mmol) were combined. After workup and purification by “catch and release,” the title compound was obtained as a slightly yellow solid (0.0450 g, 59%). 1H-NMR (CDCl3): δ 7.65-7.60 (m, 2H), 7.51-7.46 (m, 1H), 7.44-7.39 (m, 2H), 7.36 (dd, J=4.8 Hz, J=9.2 Hz, 1H), 7.33-7.26 (m, 1H), 7.03 (dd, J=2.4 Hz, J=8.4 Hz, 1H), 4.48 (s, 1H), 3.45 (s, 3H), 2.30-1.60 (br s, 2H). MS (ESI) (M+H)+=284.

Workup

  1. customAfter workup and purification by “

Sources & evidence

ORD record
ord-b73792d584914f90bcae3c42fe154e08
Source dataset
uspto-grants-2008_05
Patent number
US07375101B2

Reaction notes

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