N'-(3-Cyano-6-methyl-pyridin-2-yl)-N,N-dimethyl-formamidine → HCID 67040431, compound

HRID 605091Notes

Reaction equation

HRID 605091 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][CH:11]=[C:10]([Br:14])[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.NC1C=C(C=CC=1OC1C=CC(O)=CC=1)C(NC1C=CC(Br)=CC=1)=O>>[Br:14][C:10]1[CH:9]=[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:13]=[CH:12][CH:11]=1

Participants

4

Reactant 3

HCID 66808573N'-(3-Cyano-6-methyl-pyridin-2-yl)-N,N-dimethyl-formamidine2×HCID 67040735HCID 67040735, compoundHCID 67040854HCID 67040854, compound2×

Product 1

HCID 67040431HCID 67040431, compoundYield 75%

Procedure

The product of Example 39A was reacted with the product of Example 9B using the procedure of Example 37D substituting the product of Example 39A for the product of Example 37C and substituting the product of Example 9B for 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 (32 mg, 75%). 1H NMR (300 MHz, DMSO-D6) δ ppm: 2.67 (s, 3 H) 6.75 (d, J=8.82 Hz, 2 H) 6.82-6.98 (m, 3 H) 7.20-7.38 (m, 2 H) 7.54 (d, J=8.46 Hz, 1 H) 7.69-7.81 (m, 1 H) 7.87 (dd, J=8.64, 2.02 Hz, 1 H) 8.10 (s, 1 H) 8.19 (d, J=1.84 Hz, 1 H) 8.61 (s, 1 H) 8.78 (d, J=8.46 Hz, 1 H) 9.39 (s, 1 H) 10.01 (s, 1 H) 10.32 (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-ec6e0e8a2bdd407e83b7813741404c1a
Source dataset
uspto-grants-2011_03
Patent number
US07910595B2

Reaction notes

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