HCID 21471626, compound → HCID 178493871, compound

HRID 536255Notes

Reaction equation

HRID 536255 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].[C:30]([O:34][C:35]([NH:37][C:38]1[N:43]=[CH:42][C:41]([C:44](O)=[O:45])=[CH:40][N:39]=1)=[O:36])([CH3:33])([CH3:32])[CH3:31]>>[C:30]([O:34][C:35](=[O:36])[NH:37][C:38]1[N:43]=[CH:42][C:41]([C:44](=[O:45])[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)=[CH:40][N:39]=1)([CH3:33])([CH3:31])[CH3:32]

Participants

3

Reactant 2

HCID 21471626HCID 21471626, compoundHCID 178493873HCID 178493873, compound

Product 1

HCID 178493871HCID 178493871, 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 (Example 22, Step 1) and 2-[(tert-butoxycarbonyl)amino]pyrimidine-5-carboxylic acid. High vacuum drying gave the title compound (227 mg, 74%): HPLC MS RT=2.57 min, MH+=645.1; 1H NMR (DMSO-d6+2 drops TFA-d) δ: 1.46 (9H, s), 2.22-2.27 (2H, m), 3.15-3.18 (4H, m), 3.24-3.29 (2H, m), 3.62-3.65 (4H, m), 4.00 (3H, s), 4.20-4.27 (2H, m), 4.38 (2H, t), 4.52-4.58 (2H, m), 7.47 (1H, d), 8.03 (1H, d), 9.26 (2H, s).

Workup

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

Sources & evidence

ORD record
ord-8b2ba336cf7746cdbea5cbb2bd6a500e
Source dataset
uspto-grants-2014_10
Patent number
US08859572B2

Reaction notes

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