2-aminopyrimidine-5-carboxylic Acid → HCID 178493875, compound

HRID 536247Notes

Reaction equation

HRID 536247 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[N:33]=[CH:32][C:31]([C:34](O)=[O:35])=[CH:30][N:29]=1>>[NH2:27][C:28]1[N:33]=[CH:32][C:31]([C:34]([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:35])=[CH:30][N:29]=1

Participants

3

Reactant 2

HCID 70203672-aminopyrimidine-5-carboxylic AcidHCID 1784938763-[(5-amino-7-methoxy-2,3-dihydroimidazo[1,2-c]quinazolin-8-yl)oxy]-N,N-dimethylpropane-1-sulfonamide

Product 1

HCID 178493875HCID 178493875, 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 (Step 1) and 2-aminopyrimidine-5-carboxylic acid. High vacuum drying gave the title compound (261 mg, 79%): HPLC MS RT=2.09 min, MH+=503.2; 1H NMR (DMSO-d6+2 drops TFA-d) δ: 2.20-2.25 (2H, m), 2.78 (6H, s), 3.20-3.25 (2H, m), 3.99 (3H, s), 4.18-4.25 (2H, m), 4.37 (2H, t), 4.48-4.55 (2H, m), 7.44 (1H, d), 8.02 (1H, d), 9.07 (2H, s).

Workup

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

Sources & evidence

ORD record
ord-bcc8f14177c44687887f1518b8fcf08b
Source dataset
uspto-grants-2014_10
Patent number
US08859572B2

Reaction notes

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