1-((3-Chloropropyl)sulfonyl)-4-methylpiperazine → HCID 178481108, compound

HRID 536258Notes

Reaction equation

HRID 536258 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][CH2:26][CH2:27][S:28]([N:31]1[CH2:36][CH2:35][N:34]([CH3:37])[CH2:33][CH2:32]1)(=[O:30])=[O:29]>>[CH3:37][N:34]1[CH2:33][CH2:32][N:31]([S:28]([CH2:27][CH2:26][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)(=[O:30])=[O:29])[CH2:36][CH2:35]1

Participants

3

Reactant 2

HCID 102433851-((3-Chloropropyl)sulfonyl)-4-methylpiperazine2×HCID 178522503HCID 178522503, compound

Product 1

HCID 178481108HCID 178481108, 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-[(3-chloropropyl)sulfonyl]-4-methylpiperazine (Intermediate D) (70 mg, 16%). TLC: Rf=0.08 in 10% MeOH/CH2Cl2, HPLC MS RT=1.06 min, MH+=512.1; 1H NMR (DMSO-d6) δ: 2.12-2.37 (2H, m), 2.37 (3H, s), 3.15-3.23 (6H, m), 3.30-3.33 (4H, m), 4.00-4.20 (6H, m), 6.84 (1H, d), 7.29 (1H, s), 7.51 (1H, dd), 7.75 (1H, d), 8.41 (1H, d), 8.70 (1H, m), 9.28 (1H, s), 12.29 (1H, s).

Workup

  1. customThe procedure used for the preparation of Example 24

Sources & evidence

ORD record
ord-92ccf7066f574535ac9a1552ee173275
Source dataset
uspto-grants-2014_10
Patent number
US08859572B2

Reaction notes

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