o-Toluenesulfonyl chloride → HCID 25005935, compound

HRID 1015415Notes

Reaction equation

HRID 1015415 reaction equation
[N:1]1([C:7]2[CH:16]=[CH:15][CH:14]=[C:13]3[C:8]=2[C:9]([NH2:18])=[N:10][C:11]([NH2:17])=[N:12]3)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[C:19]1([CH3:29])[C:20]([S:25](Cl)(=[O:27])=[O:26])=[CH:21][CH:22]=[CH:23][CH:24]=1>>[C:19]1([CH3:29])[C:20]([S:25]([N:4]2[CH2:5][CH2:6][N:1]([C:7]3[CH:16]=[CH:15][CH:14]=[C:13]4[C:8]=3[C:9]([NH2:18])=[N:10][C:11]([NH2:17])=[N:12]4)[CH2:2][CH2:3]2)(=[O:27])=[O:26])=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

3

Reactant 2

HCID 8623o-Toluenesulfonyl chlorideHCID 180713185-Piperazin-1-yl-quinazoline-2,4-diamine

Product 1

HCID 25005935HCID 25005935, compoundYield 37%

Procedure

Title compound was prepared via Resin Method using 5-piperazin-1-yl-quinazoline-2,4-diamine (50 mg; 0.2 mmol) and o-toluenesulfonyl chloride (78.2 mg; 0.41 mmol) to obtain 29.3 mg. (37% yield). 1H NMR (400 MHz, DMSO-d6) δ 8.49 (br s, 1H), 7.86 (d, J=8.0 Hz, 1H), 7.61 (m, 1H), 7.73 (m, 3H), 7.47 (m, 2H), 7.38 (t, J=8.0 Hz, 1H), 6.99 (m, 2H), 6.82 (d, J=7.2 Hz, 1H), 5.93 (br s, 2H), 3.67 (d, J=12 Hz, 2H), 3.12 (d, J=12.0 Hz, 2H), 2.94 (t, J=11.5 Hz, 1H), 2.78 (t, J=11.5 Hz, 2H), 2.62 (s, 3H).

Workup

  1. customto obtain 29.3 mg

Sources & evidence

ORD record
ord-17329a52e43648a091ba9d49d975fcc9
Source dataset
uspto-grants-2011_07
Patent number
US07985755B2

Reaction notes

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