1-(Chloromethyl)-4-methanesulfonylbenzene → HCID 178432763, compound

HRID 536261Notes

Reaction equation

HRID 536261 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[C:7]3[N:8]([CH2:23][CH2:24][N:25]=3)[C:9]([NH:13][C:14]([C:16]3[S:20][C:19]([CH3:21])=[N:18][C:17]=3[CH3:22])=[O:15])=[N:10][C:11]=2[CH:12]=1.ClC[C:28]1[CH:33]=[CH:32][C:31]([S:34]([CH3:37])(=[O:36])=[O:35])=[CH:30][CH:29]=1>>[CH3:21][C:19]1[S:20][C:16]([C:14]([NH:13][C:9]2[N:8]3[CH2:23][CH2:24][N:25]=[C:7]3[C:6]3[CH:5]=[CH:4][C:3]([O:2][CH2:1][C:28]4[CH:33]=[CH:32][C:31]([S:34]([CH3:37])(=[O:36])=[O:35])=[CH:30][CH:29]=4)=[CH:12][C:11]=3[N:10]=2)=[O:15])=[C:17]([CH3:22])[N:18]=1

Participants

3

Reactant 2

HCID 1235301-(Chloromethyl)-4-methanesulfonylbenzeneHCID 178487303HCID 178487303, compound

Product 1

HCID 178432763HCID 178432763, compound

Procedure

The procedure used for the preparation of Example 24, Step 2 was used to prepare the title compound from N-(8-hydroxy-2,3-dihydroimidazo[1,2-c]quinazolin-5-yl)-2,4-dimethyl-1,3-thiazole-5-carboxamide (Step 1) and 1-(chloromethyl)-4-(methylsulfonyl)benzene (15 mg, 51%). TLC: Rf 0.93 in 10% MeOH/CH2Cl2, HPLC MS RT=2.27 min, MH+=510.1; 1H NMR (DMSO-d6) δ: 2.80 (3H, s), 2.86 (3H, s), 3.39 (3H, s), 4.30-4.35 (2H, m), 4.50-4.54 (2H, m), 5.56 (2H, s), 7.39 (1H, d), 7.87 (2H, d), 7.95 (1H, s), 8.11 (2H, d), 8.50 (1H, d).

Workup

  1. customThe procedure used for the preparation of Example 24, Step 2

Sources & evidence

ORD record
ord-e0306a45323240d08e4cb27afd32c216
Source dataset
uspto-grants-2014_10
Patent number
US08859572B2

Reaction notes

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