N-(3-Aminopropyl)morpholine → HCID 86599909, compound

HRID 888026Notes

Reaction equation

[C:1]([O:5][NH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[NH:13][C:14](=[O:31])[C:15]1[CH:20]=[CH:19][C:18]([C:21]2[N:26]=[C:25](S(C)(=O)=O)[N:24]=[CH:23][CH:22]=2)=[CH:17][CH:16]=1)([CH3:4])([CH3:3])[CH3:2].NCCC[N:36]1[CH2:41][CH2:40][O:39][CH2:38][CH2:37]1>C1COCC1.CN(C)C(=O)C>[C:1]([O:5][NH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[NH:13][C:14](=[O:31])[C:15]1[CH:20]=[CH:19][C:18]([C:21]2[N:26]=[C:25]([CH2:9][CH2:8][CH2:7][NH:6][N:36]3[CH2:37][CH2:38][O:39][CH2:40][CH2:41]3)[N:24]=[CH:23][CH:22]=2)=[CH:17][CH:16]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 50 °C

Procedure

N-(2-t-Butoxyaminophenyl)-4-(2-methylsulfonyl-pyrimidin-6-yl)benzamide (Method 21, 62.5 mg, 0.133 mmol) was dissolved in a mixture of THF (2 ml) and N,N-dimethylacetamide (2 ml) and N-(3-aminopropyl)morpholine (60 μl 0.411 mmol) added. The reaction mixture was heated to 50° C. and stirred for 2 hours. The reaction mixture was then cooled and solvents removed under reduced pressure. The resultant oil was purified by elution through silica with a 5% methanol in dichloromethane, to yield the title compound as a colourless solid (65 mg, 92%); NMR Spectrum: (DMSO-d6) 1.45 (s, 9H), 1.74 (m, 2H), 2.37 (m, 6H), 3.40 (br, 2H), 3.59 (m, 4H), 7.20 (m, 2H), 7.23 (d, 1H), 7.34 (t, 1H), 7.57 (d, 1H), 8.08 (d, 2H), 8.26 (d, 2H), 8.40 (m, 1H), 8.72 (s, 1H), 9.94 (s, 1H); Mass Spectrum: M+H+ 534.

Workup

additionadded
temperatureThe reaction mixture was then cooled
customsolvents removed under reduced pressure
customThe resultant oil was purified by elution through silica with a 5% methanol in dichloromethane

Sources & evidence

ORD record: ord-859b48dedc06468f8a85a2de09709fc0
Source dataset: uspto-grants-2012_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08247562B2

Reaction notes

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