3-chloro-N,N-dimethylpropane-1-sulfonamide → 3-[(5-amino-7-methoxy-2,3-dihydroimidazo[1,2-c]quinazolin-8-yl)oxy]-N,N-dimethylpropane-1-sulfonamide

HRID 536246Notes

Reaction equation

HRID 536246 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]2[C:13]3[N:14]([CH2:22][CH2:23][N:24]=3)[C:15]([NH2:21])=[N:16][C:17]=2[C:18]=1[O:19][CH3:20])[C:2]1[CH:7]=CC=CC=1.ClCCC[S:29]([N:32]([CH3:34])[CH3:33])(=[O:31])=[O:30]>>[NH2:21][C:15]1[N:14]2[CH2:22][CH2:23][N:24]=[C:13]2[C:12]2[CH:11]=[CH:10][C:9]([O:8][CH2:1][CH2:2][CH2:7][S:29]([N:32]([CH3:34])[CH3:33])(=[O:31])=[O:30])=[C:18]([O:19][CH3:20])[C:17]=2[N:16]=1

Participants

3

Reactant 2

HCID 100353283-chloro-N,N-dimethylpropane-1-sulfonamide2×HCID 1784938207-methoxy-8-phenylmethoxy-2,3-dihydroimidazo[1,2-c]quinazolin-5-amine2×

Product 1

HCID 1784938763-[(5-amino-7-methoxy-2,3-dihydroimidazo[1,2-c]quinazolin-8-yl)oxy]-N,N-dimethylpropane-1-sulfonamide

Procedure

The procedure used for the preparation of Example 1 was used to prepare the title compound from 5-amino-7-methoxy-2,3-dihydroimidazo[1,2-c]quinazolin-8-ol bistrifluoroacetate salt (Intermediate A) and 3-chloro-N,N-dimethylpropane-1-sulfonamide (Intermediate F). High vacuum drying gave the title compound (1.12 g, 86%): HPLC MS RT=1.28 min, MH+=382.2; 1H NMR (DMSO-d6+2 drops TFA-d) δ: 2.15-2.20 (2H, m), 2.77 (6H, s), 3.18-3.23 (2H, m), 3.84 (3H, s), 4.18-4.21 (2H, m), 4.29-4.35 (4H, m), 7.30 (1H, d), 7.90 (1H, d).

Workup

  1. customThe procedure used for the preparation of Example 1

Sources & evidence

ORD record
ord-8d3d7898108644aabbaa6ae628a815f7
Source dataset
uspto-grants-2014_10
Patent number
US08859572B2

Reaction notes

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