Thiophosgene → HCID 59713943, compound

HRID 2223076Notes

Reaction equation

[NH2:1][CH:2]1[N:8]=[C:7]([C:9]2[C:10]([O:17][CH3:18])=[N:11][C:12]([O:15][CH3:16])=[N:13][CH:14]=2)[C:6]2[CH:19]=[C:20]([Cl:23])[CH:21]=[CH:22][C:5]=2[N:4]([CH3:24])[C:3]1=[O:25].[C:26](Cl)(Cl)=[S:27]>>[Cl:23][C:20]1[CH:21]=[CH:22][C:5]2[N:4]([CH3:24])[C:3](=[O:25])[CH:2]([N:1]=[C:26]=[S:27])[N:8]=[C:7]([C:9]3[C:10]([O:17][CH3:18])=[N:11][C:12]([O:15][CH3:16])=[N:13][CH:14]=3)[C:6]=2[CH:19]=1

Participants

Reactant 2

HCID 10040Thiophosgene

HCID 59713713HCID 59713713, compound

Product 1

HCID 59713943HCID 59713943, compoundYield 44%

Procedure

As illustrated in the scheme above and following General Procedure 2, 3-amino-7-chloro-5-(2,4-dimethoxy-5-pyrimidinyl)-1,3-dihydro-1-methyl-2H-1,4-benzodiazepin-2-one (1.15 g, 3.18 mmol) and thiophosgene (0.49 mL, 6.4 mmol) were combined. Purification of the crude product by silica gel column chromatography (9:1 CH2Cl2:EtOAc) provided the title compound as a viscous dark yellow oil (0.560 g, 44%). 1H-NMR (CDCl3): δ 8.60 (s, 1H), 7.55 (dd, J=2.5 Hz, J=8.8 Hz, 1H), 7.33 (d, J=8.8 Hz, 1H), 7.17 (d, J=2.5 Hz, 1H), 5.16 (s, 1H), 4.07 (s, 3H), 3.78 (s, 3H), 3.49 (s, 3H). MS (ESI) (M+H)+=404.

Workup

customPurification of the crude product by silica gel column chromatography (9:1 CH2Cl2:EtOAc)

Sources & evidence

ORD record: ord-47120a7f3f3d46c89b9364729d707ca3
Source dataset: uspto-grants-2008_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07375101B2

Reaction notes

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