Diisopropylethylamine → 5-(2-chlorophenyl)-1-(2,6-dichlorophenyl)-7-{[4-(2-pyrrolidin-1-ylethyl)piperazin-1-yl]sulfonyl}-3,4-dihydroquinazolin-2(1H)-one

HRID 394201Notes

Reaction equation

HRID 394201 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:17]=[C:16]([S:18](Cl)(=[O:20])=[O:19])[CH:15]=[C:14]2[C:9]=1[CH2:10][NH:11][C:12](=[O:30])[N:13]2[C:22]1[C:27]([Cl:28])=[CH:26][CH:25]=[CH:24][C:23]=1[Cl:29].[N:31]1([CH2:36][CH2:37][N:38]2[CH2:43][CH2:42][NH:41][CH2:40][CH2:39]2)[CH2:35][CH2:34][CH2:33][CH2:32]1.C(N(C(C)C)CC)(C)C>>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:17]=[C:16]([S:18]([N:41]2[CH2:40][CH2:39][N:38]([CH2:37][CH2:36][N:31]3[CH2:32][CH2:33][CH2:34][CH2:35]3)[CH2:43][CH2:42]2)(=[O:20])=[O:19])[CH:15]=[C:14]2[C:9]=1[CH2:10][NH:11][C:12](=[O:30])[N:13]2[C:22]1[C:27]([Cl:28])=[CH:26][CH:25]=[CH:24][C:23]=1[Cl:29]

Participants

4

Reactant 3

HCID 81531DiisopropylethylamineHCID 27372501-[2-(Pyrrolidin-1-yl)ethyl]piperazineHCID 226481335-(2-Chlorophenyl)-1-(2,6-dichlorophenyl)-2-oxo-1,2,3,4-tetrahydroquinazoline-7-sulfonyl chloride

Product 1

HCID 102116425-(2-chlorophenyl)-1-(2,6-dichlorophenyl)-7-{[4-(2-pyrrolidin-1-ylethyl)piperazin-1-yl]sulfonyl}-3,4-dihydroquinazolin-2(1H)-one

Procedure

The 5-(2-chlorophenyl)-1-(2,6-dichlorophenyl)-7-{[4-(2-pyrrolidin-1-ylethyl)piperazin-1-yl]sulfonyl}-3,4-dihydroquinazolin-2(1H)-one was prepared from 5-(2-chlorophenyl)-1-(2,6-dichlorophenyl)-2-oxo-1,2,3,4-tetrahydroquinazoline-7-sulfonyl chloride and 1-(2-pyrrolidin-1-ylethyl)piperazine by a procedure analogous to that described in EXAMPLE CCC23, STEP A, except that no diisopropylethylamine was used. Mass spectrum (ESI) 648 (M+1). 1H NMR (500 MHz, CDCl3): selected peaks δ 1.81 (brs, 4H); 2.58 (m, 12H); 3.00 (brs, 4H); 4.35 (dd, J=15.4 Hz, J=1.6 Hz, 1 H); 4.46 (dd, J=15.4 Hz, J=1.6 Hz, 1H).

Sources & evidence

ORD record
ord-99cc29428c36453e99959972e6519d2e
Source dataset
uspto-grants-2004_10
Patent number
US06809199B2

Reaction notes

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