6-Aminonicotinic acid → HCID 178493874, compound

HRID 536248Notes

Reaction equation

HRID 536248 reaction equation
[NH2:1][C:2]1[N:11]2[CH2:12][CH2:13][N:14]=[C:10]2[C:9]2[CH:8]=[CH:7][C:6]([O:15][CH2:16][CH2:17][CH2:18][S:19]([N:22]([CH3:24])[CH3:23])(=[O:21])=[O:20])=[C:5]([O:25][CH3:26])[C:4]=2[N:3]=1.[NH2:27][C:28]1[CH:36]=[CH:35][C:31]([C:32](O)=[O:33])=[CH:30][N:29]=1>>[NH2:27][C:28]1[CH:36]=[CH:35][C:31]([C:32]([NH:1][C:2]2[N:11]3[CH2:12][CH2:13][N:14]=[C:10]3[C:9]3[CH:8]=[CH:7][C:6]([O:15][CH2:16][CH2:17][CH2:18][S:19]([N:22]([CH3:24])[CH3:23])(=[O:20])=[O:21])=[C:5]([O:25][CH3:26])[C:4]=3[N:3]=2)=[O:33])=[CH:30][N:29]=1

Participants

3

Reactant 2

HCID 184966-Aminonicotinic acidHCID 1784938763-[(5-amino-7-methoxy-2,3-dihydroimidazo[1,2-c]quinazolin-8-yl)oxy]-N,N-dimethylpropane-1-sulfonamide

Product 1

HCID 178493874HCID 178493874, compound

Procedure

The procedure used for the preparation of Example 16, Step 2 was used to prepare the title compound from 3-[(5-amino-7-methoxy-2,3-dihydroimidazo[1,2-c]quinazolin-8-yl)oxy]-N,N-dimethylpropane-1-sulfonamide (Example 17 Step 1) and 6-aminonicotinic acid. High vacuum drying gave the title compound (117 mg, 59%): HPLC MS RT=1.60 min, MH+=502.2; 1H NMR (DMSO-d6+2 drops TFA-d) δ: 2.19-2.24 (2H, m), 2.78 (6H, s), 3.19-3.24 (2H, m), 3.99 (3H, s), 4.20-4.26 (2H, m), 4.37 (2H, t), 4.47-4.54 (2H, m), 7.04 (1H, d), 7.46 (1H, d), 8.03 (1H, d), 8.48 (1H, dd), 8.77 (1H, d).

Workup

  1. customThe procedure used for the preparation of Example 16, Step 2

Sources & evidence

ORD record
ord-db36ecb6372049efa32df678d68c5ac6
Source dataset
uspto-grants-2014_10
Patent number
US08859572B2

Reaction notes

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