2-aminopyrimidine-5-carboxylic Acid → HCID 178493864, compound

HRID 536252Notes

Reaction equation

HRID 536252 reaction equation
[O:1]=[S:2]1(=[O:28])[CH2:7][CH2:6][N:5]([CH2:8][CH2:9][CH2:10][O:11][C:12]2[CH:13]=[CH:14][C:15]3[C:16]4[N:17]([CH2:25][CH2:26][N:27]=4)[C:18]([NH2:24])=[N:19][C:20]=3[C:21]=2[O:22][CH3:23])[CH2:4][CH2:3]1.[NH2:29][C:30]1[N:35]=[CH:34][C:33]([C:36](O)=[O:37])=[CH:32][N:31]=1>>[NH2:29][C:30]1[N:35]=[CH:34][C:33]([C:36]([NH:24][C:18]2[N:17]3[CH2:25][CH2:26][N:27]=[C:16]3[C:15]3[CH:14]=[CH:13][C:12]([O:11][CH2:10][CH2:9][CH2:8][N:5]4[CH2:6][CH2:7][S:2](=[O:1])(=[O:28])[CH2:3][CH2:4]4)=[C:21]([O:22][CH3:23])[C:20]=3[N:19]=2)=[O:37])=[CH:32][N:31]=1

Participants

3

Reactant 2

HCID 70203672-aminopyrimidine-5-carboxylic AcidHCID 1784938658-[3-(1,1-dioxo-1,4-thiazinan-4-yl)propoxy]-7-methoxy-2,3-dihydroimidazo[1,2-c]quinazolin-5-amine

Product 1

HCID 178493864HCID 178493864, compound

Procedure

The procedure used for the preparation of Example 16, Step 2 was used to prepare the title compound from 8-[3-(1,1-dioxidothiomorpholin-4-yl)propoxy]-7-methoxy-2,3-dihydroimidazo[1,2-c]quinazolin-5-amine (Example 19, Step 1) and 2-aminopyrimidine-5-carboxylic acid. High vacuum drying at 60° C. gave the title compound (272 mg, 79%): HPLC MS RT=1.45 min, MH+=529.2; 1H NMR (DMSO-d6+2 drops TFA-d) δ: 2.25-2.30 (2H, m), 3.44-3.49 (2H, m), 3.61-3.63 (4H, m), 3.83 (4H, bs), 3.99 (3H, s), 4.18-4.25 (2H, m), 4.33 (2H, t), 4.48-4.55 (2H, m), 7.43 (1H, d), 8.02 (1H, d), 9.04 (2H, s).

Workup

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

Sources & evidence

ORD record
ord-78ef9f60311d4df2905460723a8dd63f
Source dataset
uspto-grants-2014_10
Patent number
US08859572B2

Reaction notes

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