1,3,4-Thiadiazol-2-amine → 4-(4-chloro-2-methoxyphenyl)-N-(1,3,4-thiadiazol-2-yl)quinazoline-7-sulfonamide

HRID 1473691Notes

Reaction equation

HRID 1473691 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:17]3[C:12](=[CH:13][C:14]([S:18]([O:21]C4C(F)=C(F)C(F)=C(F)C=4F)(=O)=[O:19])=[CH:15][CH:16]=3)[N:11]=[CH:10][N:9]=2)=[C:4]([O:33][CH3:34])[CH:3]=1.[S:35]1[CH:39]=[N:38][N:37]=[C:36]1[NH2:40].ClC1C=C(C2C3C(=CC(S(OC4C(F)=C(F)C(F)=C(F)C=4F)(=O)=O)=CC=3)N=CN=2)C(OC)=CC=1C1C=CC=C(F)C=1.S1C(N)=NC=N1>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:17]3[C:12](=[CH:13][C:14]([S:18]([NH:40][C:36]4[S:35][CH:39]=[N:38][N:37]=4)(=[O:21])=[O:19])=[CH:15][CH:16]=3)[N:11]=[CH:10][N:9]=2)=[C:4]([O:33][CH3:34])[CH:3]=1

Participants

5

Reactant 4

HCID 199091,3,4-Thiadiazol-2-amineHCID 2902745-Amino-1,2,4-thiadiazoleHCID 86687767Perfluorophenyl 4-(2-chloro-3'-fluoro-5-methoxy-[1,1'-biphenyl]-4-yl)quinazoline-7-sulfonateHCID 86687771Perfluorophenyl 4-(4-chloro-2-methoxyphenyl)quinazoline-7-sulfonate

Product 1

HCID 866877754-(4-chloro-2-methoxyphenyl)-N-(1,3,4-thiadiazol-2-yl)quinazoline-7-sulfonamide

Procedure

The title compound was prepared in an analogous manner to that of EXAMPLE 521, except that perfluorophenyl 4-(4-chloro-2-methoxyphenyl)quinazoline-7-sulfonate and 1,3,4-thiadiazol-2-amine were used instead of perfluorophenyl 4-(2-chloro-3′-fluoro-5-methoxy-[1,1′-biphenyl]-4-yl)quinazoline-7-sulfonate and 1,2,4-thiadiazol-5-amine to afford 4-(4-chloro-2-methoxyphenyl)-N-(1,3,4-thiadiazol-2-yl)quinazoline-7-sulfonamide as a yellow solid. (ESI) 434.1 (M+H)+.

Workup

  1. customThe title compound was prepared in an analogous manner to that of EXAMPLE 521

Sources & evidence

ORD record
ord-7b704934cf154fccbef12699c86580a9
Source dataset
uspto-grants-2015_04
Patent number
US09012443B2

Reaction notes

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