1-((3-Chloropropyl)sulfonyl)-4-methylpiperazine → HCID 178481110, compound

HRID 536242Notes

Reaction equation

HRID 536242 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][C:3]=1[O:24][CH2:25][CH2:26][CH2:27][N:28]1[CH2:33][CH2:32][O:31][CH2:30][CH2:29]1.Cl[CH2:35][CH2:36][CH2:37][S:38]([N:41]1[CH2:46][CH2:45][N:44]([CH3:47])[CH2:43][CH2:42]1)(=[O:40])=[O:39]>>[CH3:47][N:44]1[CH2:43][CH2:42][N:41]([S:38]([CH2:37][CH2:36][CH2:35][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][C:3]=2[O:24][CH2:25][CH2:26][CH2:27][N:28]2[CH2:29][CH2:30][O:31][CH2:32][CH2:33]2)(=[O:40])=[O:39])[CH2:46][CH2:45]1

Participants

3

Reactant 2

HCID 102433851-((3-Chloropropyl)sulfonyl)-4-methylpiperazine2×HCID 178522494HCID 178522494, compound2×

Product 1

HCID 178481110HCID 178481110, compound

Procedure

The procedure used for the preparation of Example 1 was used to prepare the title compound from N-[7-hydroxy-8-(3-morpholin-4-ylpropoxy)-2,3-dihydroimidazo[1,2-c]quinazolin-5-yl]nicotinamide (Intermediate H) and 1-[(3-chloropropyl)sulfonyl]-4-methylpiperazine (Intermediate D). High vacuum drying gave the title compound (29 mg, 27%): HPLC MS RT=0.23 min, MH+=655.6; 1H NMR (DMSO-d6+2 drops TFA-d) δ: 2.22-2.27 (4H, m), 2.82 (3H, s), 3.09-3.18 (6H, m), 3.29-3.32 (2H, m), 3.45-3.52 (6H, m), 3.64-3.70 (2H, m), 3.77-3.80 (2H, m), 3.99-4.01 (2H, m), 4.24-4.29 (2H, m), 4.32-4.36 (4H, m), 4.55-4.60 (2H, m), 7.49 (1H, d), 7.90 (1H, dd), 8.09 (1H, d), 8.83 (1H, d), 8.98 (1H, dd), 9.47 (1H, d).

Workup

  1. customThe procedure used for the preparation of Example 1

Sources & evidence

ORD record
ord-23cabd12e2fb42fb9796c444905c2a6e
Source dataset
uspto-grants-2014_10
Patent number
US08859572B2

Reaction notes

Loading…