Triphenylphosphine → HCID 59713977, compound

HRID 2223079Notes

Reaction equation

[N:1]([CH:4]1[N:10]=[C:9]([C:11]2[CH:15]=[CH:14][S:13][CH:12]=2)[C:8]2[CH:16]=[C:17]([Cl:20])[CH:18]=[CH:19][C:7]=2[N:6]([CH3:21])[C:5]1=[O:22])=[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:15]=[CH:14][S:13][CH:12]=2)[C:8]2[CH:16]=[C:17]([Cl:20])[CH:18]=[CH:19][C:7]=2[N:6]([CH3:21])[C:5]1=[O:22]

Participants

Reactant 2

HCID 11776Triphenylphosphine

HCID 59714395HCID 59714395, compound

Product 1

HCID 59713977HCID 59713977, compound

Procedure

As illustrated in the scheme above and following General Procedure 7, 3-azido-7-chloro-1,3-dihydro-1-methyl-5-(3-thienyl)-2H-1,4-benzodiazepin-2-one (1.60 g, 4.82 mmol) and PS—PPh3 (30.0 g of 1.37 mmol/g, 41.1 mmol) were combined. After workup and purification by “catch and release,” the title compound was obtained as a brown solid (1.35 g, 92%). 1H-NMR (CDCl3): δ 7.56-7.50 (m, 4H), 7.36 (dd, J=3.1 Hz, J=4.9 Hz, 1H), 7.29 (d, J=8.8 Hz, 1H), 4.46 (s, 1H), 3.43 (s, 3H), 2.35-2.15 (br s, 2H). MS (ESI) (M+H)+=306.

Workup

customAfter workup and purification by “

Sources & evidence

ORD record: ord-60c6dff75efd4b5ca4df02b610e48eeb
Source dataset: uspto-grants-2008_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07375101B2

Reaction notes

Loading…