Diisopropylethylamine → HCID 178474220, compound

HRID 1787557Notes

Reaction equation

Br.[N:2]1([C:8]2[CH:9]=[CH:10][C:11]3[C:12]4[N:13]([CH2:19][CH2:20][N:21]=4)[C:14]([NH2:18])=[N:15][C:16]=3[CH:17]=2)[CH2:7][CH2:6][O:5][CH2:4][CH2:3]1.[C:22]([NH:25][C:26]1[CH:34]=[CH:33][C:29]([C:30](O)=[O:31])=[CH:28][N:27]=1)(=[O:24])[CH3:23].C(N(CC)C(C)C)(C)C.C([O-])(O)=O.[Na+]>CN(C)C=O>[C:22]([NH:25][C:26]1[CH:34]=[CH:33][C:29]([C:30]([NH:18][C:14]2[N:13]3[CH2:19][CH2:20][N:21]=[C:12]3[C:11]3[CH:10]=[CH:9][C:8]([N:2]4[CH2:7][CH2:6][O:5][CH2:4][CH2:3]4)=[CH:17][C:16]=3[N:15]=2)=[O:31])=[CH:28][N:27]=1)(=[O:24])[CH3:23]

Participants

Conditions

Temperature: 90 °C

Procedure

To a mixture of 8-(morpholin-4-yl)-2,3-dihydroimidazo[1,2-c]quinazolin-5-amine hydrobromide 105.7 mg (0.30 mmol), 6-(acetamido)nicotinic acid 81.1 mg (0.45 mmol) and N,N-diisopropylethylamine 0.26 mL (1.50 mmol) in N,N-dimethylformamide 2 mL was added PyBOP((1H-1,2,3-benzotriazol-1-yloxy)(tripyrrolidin-1-yl)-phosphonium hexafluorophosphate) 234.2 mg (0.45 mmol) and stirred at 90° C. for 16 hours. After cooling to room temperature, saturated NaHCO3 solution was added. The precipitate was collected and washed with water, methanol, and diethyl ether to give the title compound 41.1 mg as yellow solid. Yield 31.6%.

Workup

temperatureAfter cooling to room temperature
customThe precipitate was collected
washwashed with water, methanol, and diethyl ether

Sources & evidence

ORD record: ord-4cb9f5ffb60e4973b48f0fd65fd117a7
Source dataset: uspto-grants-2009_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07511041B2

Reaction notes

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