6-Aminonicotinic acid → HCID 178493822, compound

HRID 536251Notes

Reaction equation

HRID 536251 reaction equation
[CH3:1][O:2][C:3]1[C:12]2[N:11]=[C:10]([NH2:13])[N:9]3[CH2:14][CH2:15][N:16]=[C:8]3[C:7]=2[CH:6]=[CH:5][C:4]=1[O:17][CH2:18][C:19]1[CH:24]=[CH:23][C:22]([S:25]([CH3:28])(=[O:27])=[O:26])=[CH:21][CH:20]=1.[NH2:29][C:30]1[CH:38]=[CH:37][C:33]([C:34](O)=[O:35])=[CH:32][N:31]=1>>[NH2:29][C:30]1[CH:38]=[CH:37][C:33]([C:34]([NH:13][C:10]2[N:9]3[CH2:14][CH2:15][N:16]=[C:8]3[C:7]3[CH:6]=[CH:5][C:4]([O:17][CH2:18][C:19]4[CH:24]=[CH:23][C:22]([S:25]([CH3:28])(=[O:27])=[O:26])=[CH:21][CH:20]=4)=[C:3]([O:2][CH3:1])[C:12]=3[N:11]=2)=[O:35])=[CH:32][N:31]=1

Participants

3

Reactant 2

HCID 184966-Aminonicotinic acidHCID 178493824HCID 178493824, compound

Product 1

HCID 178493822HCID 178493822, compound

Procedure

The procedure used for the preparation of Example 16, Step 2 was used to prepare the title compound from 7-methoxy-8-{[4-(methylsulfonyl)benzyl]oxy}-2,3-dihydroimidazo[1,2-c]quinazolin-5-amine (Example 16 Step 1) and 6-aminonicotinic acid. High vacuum drying gave the title compound (151 mg, 77%): HPLC MS RT=2.00 min, MH+=521.1; 1H NMR (DMSO-d6+2 drops TFA-d) δ: 3.24 (3H, s), 4.02 (3H, s), 4.23-4.28 (2H, m), 4.50-4.55 (2H, m), 5.56 (2H, s), 7.06 (1H, d), 7.58 (1H, d), 7.79 (2H, d), 8.01 (1H, d), 8.05 (1H, d), 8.50 (1H, dd), 8.79 (1H, d).

Workup

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

Sources & evidence

ORD record
ord-81fd1ebe0f15478dbfff2165e2f6b265
Source dataset
uspto-grants-2014_10
Patent number
US08859572B2

Reaction notes

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