6-Aminonicotinic acid → HCID 178507639, compound

HRID 536265Notes

Reaction equation

HRID 536265 reaction equation
[N:1]1([S:7]([CH2:10][CH2:11][CH2:12][O:13][C:14]2[CH:15]=[CH:16][C:17]3[C:18]4[N:19]([CH2:25][CH2:26][N:27]=4)[C:20]([NH2:24])=[N:21][C:22]=3[CH:23]=2)(=[O:9])=[O:8])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[NH2:28][C:29]1[CH:37]=[CH:36][C:32]([C:33](O)=[O:34])=[CH:31][N:30]=1>>[NH2:28][C:29]1[CH:37]=[CH:36][C:32]([C:33]([NH:24][C:20]2[N:19]3[CH2:25][CH2:26][N:27]=[C:18]3[C:17]3[CH:16]=[CH:15][C:14]([O:13][CH2:12][CH2:11][CH2:10][S:7]([N:1]4[CH2:6][CH2:5][O:4][CH2:3][CH2:2]4)(=[O:8])=[O:9])=[CH:23][C:22]=3[N:21]=2)=[O:34])=[CH:31][N:30]=1

Participants

3

Reactant 2

HCID 184966-Aminonicotinic acidHCID 178508203HCID 178508203, compound

Product 1

HCID 178507639HCID 178507639, compound

Procedure

The procedure used for the preparation of Example 28, Step 2 was used to prepare the title compound from 8-[3-(morpholin-4-ylsulfonyl)propoxy]-2,3-dihydroimidazo[1,2-c]quinazolin-5-amine (Example 28, Step 1) and 6-aminonicotinic acid. Yield 50.0 mg (14%). TLC Rf=0.52 in 10% MeOH/CH2Cl2, HPLC MS RT=0.23 min, MH+=514.4; 1H NMR (MeOD) δ: 2.35 (2H, m), 3.20-3.33 (6H, m), 3.72 (4H, m), 4.26 (2H, t), 4.35 (2H, t), 4.63 (2H, t), 7.06 (1H, d), 7.19 (1H, dd), 7.36 (1H, s), 8.04 (1H, d), 8.56 (1H, dd), 8.74 (1H, s).

Workup

  1. customThe procedure used for the preparation of Example 28, Step 2

Sources & evidence

ORD record
ord-41a50ecf571b4a82a0444206c62feb72
Source dataset
uspto-grants-2014_10
Patent number
US08859572B2

Reaction notes

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