Pivaloyl chloride → N-{5-(acetylamino)-2-[(tetrahydro-2H-pyran-4-ylmethyl)amino]phenyl}-2,2-dimethylpropanamide

HRID 1435407Notes

Reaction equation

[NH2:1][C:2]1[CH:3]=[C:4]([NH:16][C:17](=[O:19])[CH3:18])[CH:5]=[CH:6][C:7]=1[NH:8][CH2:9][CH:10]1[CH2:15][CH2:14][O:13][CH2:12][CH2:11]1.CCN(C(C)C)C(C)C.[CH3:29][C:30]([CH3:35])([CH3:34])[C:31](Cl)=[O:32]>C(Cl)Cl>[C:17]([NH:16][C:4]1[CH:5]=[CH:6][C:7]([NH:8][CH2:9][CH:10]2[CH2:11][CH2:12][O:13][CH2:14][CH2:15]2)=[C:2]([NH:1][C:31](=[O:32])[C:30]([CH3:35])([CH3:34])[CH3:29])[CH:3]=1)(=[O:19])[CH3:18]

Participants

Conditions

Temperature: 0 °C

Procedure

N-{3-Amino-4-[(tetrahydro-2H-pyran-4-ylmethyl)amino]phenyl}acetamide (25.9 g, 98.6 mmol) and DIPEA (20.6 mL, 15.4 g, 118 mmol) were dissolved in 500 mL of DCM. Trimethylacetyl chloride (12.7 mL, 12.5 g, 103 mmol) was added dropwise at 0° C. and the solution was stirred for 3 h at 0° C. and 1 h at room temperature. The pink solid was collected by filtration, washed with H2O and dried in vacuo. Yield: 33.1 g (97%); MS (ESI) (M+H)+=348.05.

Workup

filtrationThe pink solid was collected by filtration
washwashed with H2O
customdried in vacuo

Sources & evidence

ORD record: ord-f1ecf0e1815840f18368428df59134f9
Source dataset: uspto-grants-2009_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07615642B2

Reaction notes

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