tert-Butoxy bis(dimethylamino)methane → (E)-6-(bis(4-methoxybenzyl)amino)-4-(2-(dimethylamino)vinyl)nicotinonitrile

HRID 874689

Reaction equation

[CH3:1][O:2][C:3]1[CH:28]=[CH:27][C:6]([CH2:7][N:8]([CH2:18][C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=2)[C:9]2[CH:16]=[C:15]([CH3:17])[C:12]([C:13]#[N:14])=[CH:11][N:10]=2)=[CH:5][CH:4]=1.C(O[CH:34](N(C)C)[N:35]([CH3:37])[CH3:36])(C)(C)C>CN(C)C=O>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][N:8]([CH2:18][C:19]2[CH:20]=[CH:21][C:22]([O:25][CH3:26])=[CH:23][CH:24]=2)[C:9]2[CH:16]=[C:15](/[CH:17]=[CH:34]/[N:35]([CH3:37])[CH3:36])[C:12]([C:13]#[N:14])=[CH:11][N:10]=2)=[CH:27][CH:28]=1

Participants

Conditions

Temperature: 70 °C

Procedure

A mixture of 4-3 (7.20 g, 19.3 mmol), tert-butoxy bis(dimethylamino)methane (16.0 mL, 77.5 mmol), and N,N-dimethylformamide (5.40 mL) was stirred at 70° C. for 16 hours under an atmosphere of nitrogen gas. The reaction mixture was concentrated under reduced pressure to give 9.40 g of 4-4 as a brown oil. The crude product was used for next step without further purification.

Workup

concentrationThe reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record: ord-7308b08ea5f341f3a4a2a44cbb67045a
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08980916B2

Linked notes

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