3-chloro-N,N-dimethylpropane-1-sulfonamide → HCID 178486162, compound

HRID 536243Notes

Reaction equation

HRID 536243 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]([CH3:43])[CH3:42])(=[O:40])=[O:39]>>[CH3:42][N:41]([CH3:43])[S:38]([CH2:37][CH2:36][CH2:35][O: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[CH2:29][CH2:30][O:31][CH2:32][CH2:33]1)(=[O:40])=[O:39]

Participants

3

Reactant 2

HCID 100353283-chloro-N,N-dimethylpropane-1-sulfonamide2×HCID 178522494HCID 178522494, compound2×

Product 1

HCID 178486162HCID 178486162, 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 3-chloro-N,N-dimethylpropane-1-sulfonamide (Intermediate F). High vacuum drying gave the title compound (15 mg, 15%): HPLC MS RT=0.24 min, MH+=600.4; 1H NMR (DMSO-d6+2 drops TFA-d) δ: 1.07 (6H, t), 2.18-2.27 (4H, m), 3.04-3.13 (2H, m), 3.27-3.36 (4H, q), 3.51 (2H, d), 3.66 (2H, t), 3.98-4.02 (2H, m), 4.21-4.36 (6H, m), 4.56-4.59 (2H, m), 7.49 (1H, d), 8.02 (1H, dd), 8.08 (1H, d), 8.96 (1H, d), 9.04 (1H, dd), 9.50 (1H, d).

Workup

  1. customThe procedure used for the preparation of Example 1

Sources & evidence

ORD record
ord-e8715c19d1064de7b3421beef21f9258
Source dataset
uspto-grants-2014_10
Patent number
US08859572B2

Reaction notes

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