6-Aminonicotinic acid → HCID 178493870, compound

HRID 536254Notes

Reaction equation

HRID 536254 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][CH2:19][CH2:20][S:21]([N:24]1[CH2:29][CH2:28][O:27][CH2:26][CH2:25]1)(=[O:23])=[O:22].[NH2:30][C:31]1[CH:39]=[CH:38][C:34]([C:35](O)=[O:36])=[CH:33][N:32]=1>>[NH2:30][C:31]1[CH:39]=[CH:38][C:34]([C:35]([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][CH2:19][CH2:20][S:21]([N:24]4[CH2:25][CH2:26][O:27][CH2:28][CH2:29]4)(=[O:22])=[O:23])=[C:3]([O:2][CH3:1])[C:12]=3[N:11]=2)=[O:36])=[CH:33][N:32]=1

Participants

3

Reactant 2

HCID 184966-Aminonicotinic acidHCID 178493873HCID 178493873, compound

Product 1

HCID 178493870HCID 178493870, compound

Procedure

The procedure used for the preparation of Example 16, Step 2 was used to prepare the title compound from 7-methoxy-8-[3-(morpholin-4-ylsulfonyl)propoxy]-2,3-dihydroimidazo[1,2-c]quinazolin-5-amine (Step 1) and 6-aminonicotinic acid. High vacuum drying gave the title compound (122 mg, 63%): HPLC MS RT=1.96 min, MH+=544.2; 1H NMR (DMSO-d6+2 drops TFA-d) δ: 2.22-2.27 (2H, m), 3.15-3.18 (4H, m), 3.24-3.29 (2H, m), 3.61-3.65 (4H, m), 3.99 (3H, s), 4.24-4.27 (2H, m), 4.38 (2H, t), 4.48-4.52 (2H, m), 7.05 (1H, d), 7.47 (1H, d), 8.04 (1H, d), 8.49 (1H, dd), 8.78 (1H, d).

Workup

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

Sources & evidence

ORD record
ord-5b6757e3e7fc4bf2a2fca5626824f25d
Source dataset
uspto-grants-2014_10
Patent number
US08859572B2

Reaction notes

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