1-(Chloromethyl)-4-methanesulfonylbenzene → HCID 178504765, compound

HRID 536259Notes

Reaction equation

HRID 536259 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6]3[N:7]([CH2:21][CH2:22][N:23]=3)[C:8]([NH:12][C:13](=[O:20])[C:14]3[CH:19]=[CH:18][CH:17]=[N:16][CH:15]=3)=[N:9][C:10]=2[CH:11]=1.Cl[CH2:25][C:26]1[CH:31]=[CH:30][C:29]([S:32]([CH3:35])(=[O:34])=[O:33])=[CH:28][CH:27]=1>>[CH3:35][S:32]([C:29]1[CH:30]=[CH:31][C:26]([CH2:25][O:1][C:2]2[CH:3]=[CH:4][C:5]3[C:6]4[N:7]([CH2:21][CH2:22][N:23]=4)[C:8]([NH:12][C:13](=[O:20])[C:14]4[CH:19]=[CH:18][CH:17]=[N:16][CH:15]=4)=[N:9][C:10]=3[CH:11]=2)=[CH:27][CH:28]=1)(=[O:33])=[O:34]

Participants

3

Reactant 2

HCID 1235301-(Chloromethyl)-4-methanesulfonylbenzeneHCID 178522503HCID 178522503, compound

Product 1

HCID 178504765HCID 178504765, compound

Procedure

The procedure used for the preparation of Example 24 was used to prepare the title compound from N-(8-hydroxy-2,3-dihydroimidazo[1,2-c]quinazolin-5-yl)nicotinamide (Example 2-5 in WO2004029055) and 1-(chloromethyl)-4-(methylsulfonyl)benzene (20 mg, 4%). TLC: Rf=0.91 in 10% MeOH/CH2Cl2, HPLC MS RT=1.91 min, MH+=476.2; 1H NMR (DMSO-d6) δ: 3.22 (3H, s), 4.00-4.15 (4H, m), 5.33 (2H, s), 6.93 (1H, d), 7.39 (1H, s), 7.51 (1H, dd), 7.71 (2H, d), 7.78 (1H, d), 7.95 (2H, d), 8.42 (1H, d), 8.70 (1H, m), 9.29 (1H, s), 12.31 (1H, s).

Workup

  1. customThe procedure used for the preparation of Example 24

Sources & evidence

ORD record
ord-394a8a14ada949d1a1aabfc78c8c205e
Source dataset
uspto-grants-2014_10
Patent number
US08859572B2

Reaction notes

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