Triphenylphosphine → HCID 59713845, compound

HRID 2223082Notes

Reaction equation

[N:1]([CH:4]1[N:10]=[C:9]([C:11]2[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=2)[C:8]2[CH:17]=[C:18]([Cl: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]=[N:13][CH:14]=[CH:15][CH:16]=2)[C:8]2[CH:17]=[C:18]([Cl:21])[CH:19]=[CH:20][C:7]=2[N:6]([CH3:22])[C:5]1=[O:23]

Participants

Reactant 2

HCID 11776Triphenylphosphine

HCID 59713771HCID 59713771, compound

Product 1

HCID 59713845HCID 59713845, compound

Procedure

As illustrated in the scheme above and following General Procedure 7, 3-azido-7-chloro-1,3-dihydro-1-methyl-5-(3-pyridinyl)-2H-1,4-benzodiazepin-2-one (1.47 g, 4.49 mmol) and PS—PPh3 (16.4 g of 1.37 mmol/g, 22.4 mmol) were combined. After workup and purification by “catch and release,” the title compound was obtained as a slightly brown solid (1.46 g, quantitative). 1H-NMR (CDCl3): δ 8.76 (d, J=2.4 Hz, 1H), 8.72 (dd, J=1.6 Hz, J=5.2 Hz, 1H), 8.06 (dt, J=2.4 Hz, J=7.6 Hz, 1H), 7.58 (dd, J=2.4 Hz, J=8.8 Hz, 1H), 7.40 (dd, J=4.8 Hz, J=8.0 Hz, 1H), 7.35 (d, J=8.8 Hz, 1H), 7.29 (d, J=2.4 Hz, 1H), 4.51 (s, 1H), 3.46 (s, 3H), 2.41 (br s, 2H). MS (ESI) (M+H)+=301.

Workup

customAfter workup and purification by “

Sources & evidence

ORD record: ord-54985775fa78424cae98b580cd58a22f
Source dataset: uspto-grants-2008_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07375101B2

Reaction notes

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