Triphenylphosphine → HCID 59713713, compound

HRID 2223075Notes

Reaction equation

[N:1]([CH:4]1[N:10]=[C:9]([C:11]2[C:12]([O:19][CH3:20])=[N:13][C:14]([O:17][CH3:18])=[N:15][CH:16]=2)[C:8]2[CH:21]=[C:22]([Cl:25])[CH:23]=[CH:24][C:7]=2[N:6]([CH3:26])[C:5]1=[O:27])=[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[C:12]([O:19][CH3:20])=[N:13][C:14]([O:17][CH3:18])=[N:15][CH:16]=2)[C:8]2[CH:21]=[C:22]([Cl:25])[CH:23]=[CH:24][C:7]=2[N:6]([CH3:26])[C:5]1=[O:27]

Participants

Reactant 2

HCID 11776Triphenylphosphine

HCID 59713936HCID 59713936, compound

Product 1

HCID 59713713HCID 59713713, compound

Procedure

As illustrated in the scheme above and following General Procedure 7, 3-azido-7-chloro-5-(2,4-dimethoxy-5-pyrimidinyl)-1,3-dihydro-1-methyl-2H-1,4-benzodiazepin-2-one (1.22 g, 3.15 mmol) and PS—PPh3 (23.0 g of 1.37 mmol/g, 31.5 mmol) were combined. After workup and purification by “catch and release,” the title compound was obtained as a brown solid (1.15 g, quantitative). 1H-NM (CDCl3): δ 8.56 (s, 1H), 7.50 (dd, J=2.4 Hz, J=8.9 Hz, 1H), 7.30 (d, J=8.8 Hz, 1H), 7.15 (d, J=2.5 Hz, 1H), 4.46 (s, 1H), 4.06 (s, 3H), 3.77 (s, 3H), 3.46 (s, 3H), 2.85-2.12 (br s, 2H). MS (ESI) (M+H)+=362.

Workup

customAfter workup and purification by “

Sources & evidence

ORD record: ord-03532db17b2e45a2abe40df6f44736ed
Source dataset: uspto-grants-2008_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07375101B2

Reaction notes

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