Water → HCID 178493909, compound

HRID 536267Notes

Reaction equation

O[C:2]1[CH:3]=[CH:4][C:5]2[C:6]3[N:7]([CH2:23][CH2:24][N:25]=3)[C:8]([NH:14][C:15]([C:17]3[CH:18]=N[CH:20]=[N:21][CH:22]=3)=[O:16])=[N:9][C:10]=2[C:11]=1[O:12][CH3:13].[C:26](=O)([O-])[O-].[Cs+].[Cs+].CS([O:36][CH2:37][CH2:38][O:39][CH2:40][CH2:41][NH:42][C:43]([O:45][C:46]([CH3:49])([CH3:48])[CH3:47])=[O:44])(=O)=O.O>CN(C)C=O>[CH3:13][O:12][C:11]1[C:10]2[N:9]=[C:8]([NH:14][C:15]([C:17]3[CH:22]=[N:21][CH:20]=[CH:26][CH:18]=3)=[O:16])[N:7]3[CH2:23][CH2:24][N:25]=[C:6]3[C:5]=2[CH:4]=[CH:3][C:2]=1[O:36][CH2:37][CH2:38][O:39][CH2:40][CH2:41][NH:42][C:43](=[O:44])[O:45][C:46]([CH3:49])([CH3:48])[CH3:47]

Participants

Conditions

Temperature: 50 °C

Procedure

N-(8-Hydroxy-7-methoxy-2,3-dihydroimidazo[1,2-c]quinazolin-5-yl)pyrimidine-5-carboxamide (Intermediate B, 4.2 g, 7.4 mmol) was diluted in dimethylformamide (75 mL). Cesium carbonate (12.1 g, 37.1 mmol) was added, followed by 2-{2-[(tert-butoxycarbonyl)amino]ethoxy}ethyl methanesulfonate (Step 2, 5.26 g, 18.6 mmol). The mixture was stirred at 50° C. overnight. After cooling to rt, water was added and the mixture was cooled to 0° C. for 30 min. The product was isolated by vacuum filtration, washing with water, and dried in the vacuum oven. The title compound was obtained as an orange solid (3.55 g, 91%). HPLC MS RT=2.23 min, MH+=525.1. 1H NMR (DMSO-d6+2 drops TFA-d) δ: 1.35 (9H, s), 3.07 (2H, t), 3.46 (2H, t), 3.81 (2H, m), 4.02 (3H, s), 4.25 (2H, m), 4.40 (2H, m), 4.57 (2H, m), 7.49 (1H, d), 7.85 (1H, m), 8.03 (1H, d), 8.82 (1H, m), 8.93 (1H, m), 9.48 (1H, m).

Workup

temperatureAfter cooling to rt
temperaturethe mixture was cooled to 0° C. for 30 min
customThe product was isolated by vacuum filtration
washwashing with water
customdried in the vacuum oven

Sources & evidence

ORD record: ord-1a9c3a74062a4694824fa5327b34b328
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08859572B2

Reaction notes

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