1-((3-Chloropropyl)sulfonyl)-4-methylpiperazine → HCID 178481109, compound

HRID 536238Notes

Reaction equation

HRID 536238 reaction equation
[OH:1][C:2]1[C:11]2[N:10]=[C:9]([NH:12][C:13](=[O:20])[C:14]3[CH:19]=[CH:18][CH:17]=[N:16][CH:15]=3)[N:8]3[CH2:21][CH2:22][N:23]=[C:7]3[C:6]=2[CH:5]=[CH:4][CH:3]=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[C:11]3[N:10]=[C:9]([NH:12][C:13](=[O:20])[C:14]4[CH:19]=[CH:18][CH:17]=[N:16][CH:15]=4)[N:8]4[CH2:21][CH2:22][N:23]=[C:7]4[C:6]=3[CH:5]=[CH:4][CH:3]=2)(=[O:30])=[O:29])[CH2:36][CH2:35]1

Participants

3

Reactant 2

HCID 102433851-((3-Chloropropyl)sulfonyl)-4-methylpiperazine2×HCID 178522515N-(7-hydroxy-2,3-dihydroimidazo[1,2-c]quinazolin-5-yl)pyridine-3-carboxamide2×

Product 1

HCID 178481109HCID 178481109, compound

Procedure

The procedure used for the preparation of Example 1 was used to prepare the title compound from N-(7-hydroxy-2,3-dihydroimidazo[1,2-c]quinazolin-5-yl)nicotinamide (Intermediate C) and 1-[(3-chloropropyl)sulfonyl]-4-methylpiperazine (Intermediate D). High vacuum drying at 60° C. gave the title compound (72 mg, 57%): HPLC MS RT=1.22 min, MH+=512.2; 1H NMR (DMSO-d6+2 drops TFA-d) δ: 2.26-2.31 (2H, m), 2.82 (3H, s), 3.11-3.21 (4H, m), 3.45-3.50 (4H, m), 3.83-3.87 (2H, m), 4.27-4.34 (2H, m), 4.42 (2H, t), 4.58-4.65 (2H, m), 7.60 (1H, t), 7.73 (1H, d), 7.85 (1H, d), 7.94 (1H, dd), 8.86 (1H, d), 9.00 (1H, dd), 9.48 (1H, d).

Workup

  1. customThe procedure used for the preparation of Example 1

Sources & evidence

ORD record
ord-7c5c1fb74c6045b59bc8fb62e844cf25
Source dataset
uspto-grants-2014_10
Patent number
US08859572B2

Reaction notes

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