N'-(3-Cyano-6-methyl-pyridin-2-yl)-N,N-dimethyl-formamidine → HCID 67040209, compound

HRID 605089Notes

Reaction equation

HRID 605089 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:15]=[CH:16][C:17]=1[O:18][C:19]1[CH:24]=[CH:23][C:22]([OH:25])=[CH:21][CH:20]=1)[C:5]([NH:7][C:8]1[CH:13]=[CH:12][C:11]([Br:14])=[CH:10][CH:9]=1)=[O:6].C([C:28]1[C:29]([N:35]=[CH:36][N:37]([CH3:39])C)=[N:30][C:31]([CH3:34])=[CH:32][CH:33]=1)#N>>[Br:14][C:11]1[CH:12]=[CH:13][C:8]([NH:7][C:5](=[O:6])[C:4]2[CH:15]=[CH:16][C:17]([O:18][C:19]3[CH:24]=[CH:23][C:22]([OH:25])=[CH:21][CH:20]=3)=[C:2]([NH:1][C:39]3[C:28]4[CH:33]=[CH:32][C:31]([CH3:34])=[N:30][C:29]=4[N:35]=[CH:36][N:37]=3)[CH:3]=2)=[CH:9][CH:10]=1

Participants

3

Reactant 2

HCID 66808573N'-(3-Cyano-6-methyl-pyridin-2-yl)-N,N-dimethyl-formamidine2×HCID 67040735HCID 67040735, compound

Product 1

HCID 67040209HCID 67040209, compoundYield 49%

Procedure

The product of Example 37C was reacted with the product of Example 9B using the procedure of Example 37D substituting the product of Example 9B for the product of Example 8E to provide the crude title compound which was purified by column chromatography on silica gel using methanol/dichloromethane as eluent to provide the title product (42 mg, 49%). 1H NMR (300 MHz, DMSO-D6) δ ppm: 2.66 (s, 3 H) 6.75 (d, J=8.82 Hz, 2 H) 6.89 (t, J=8.27 Hz, 3 H) 7.53 (d, J=8.82 Hz, 3 H) 7.75 (d, J=9.19 Hz, 2 H) 7.86 (dd, J=8.64, 1.65 Hz, 1 H) 8.18 (d, J=1.47 Hz, 1 H) 8.61 (s, 1 H) 8.77 (d, J=8.46 Hz, 1 H) 9.39 (s, 1 H) 10.00 (s, 1 H) 10.30 (s, 1 H); MS (ESI+) m/z 542/544 (M+H)+.

Workup

  1. customto provide the crude title compound which
  2. customwas purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-685f2b44b2014a908e1a66f7db263e9f
Source dataset
uspto-grants-2011_03
Patent number
US07910595B2

Reaction notes

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