N'-(3-Cyano-6-methyl-pyridin-2-yl)-N,N-dimethyl-formamidine → HCID 67040342, compound

HRID 605152Notes

Reaction equation

HRID 605152 reaction equation
[C:1]([O:5][C:6](=[O:32])[NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([O:14][C:15]2[CH:20]=[CH:19][C:18]([C:21](=[O:30])[NH:22][C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([Br:29])[CH:24]=3)=[CH:17][C:16]=2[NH2:31])[CH:9]=1)([CH3:4])([CH3:3])[CH3:2].C([C:35]1[C:36]([N:42]=[CH:43][N:44]([CH3:46])C)=[N:37][C:38]([CH3:41])=[CH:39][CH:40]=1)#N.C(OC(=O)NC1C=CC=C(SC2C=CC(C(=O)NC3C=CC=C(Br)C=3)=CC=2N)C=1)(C)(C)C>>[C:1]([O:5][C:6](=[O:32])[NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([O:14][C:15]2[CH:20]=[CH:19][C:18]([C:21](=[O:30])[NH:22][C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([Br:29])[CH:24]=3)=[CH:17][C:16]=2[NH:31][C:46]2[C:35]3[CH:40]=[CH:39][C:38]([CH3:41])=[N:37][C:36]=3[N:42]=[CH:43][N:44]=2)[CH:9]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 3

HCID 66808573N'-(3-Cyano-6-methyl-pyridin-2-yl)-N,N-dimethyl-formamidine2×HCID 67040548HCID 67040548, compound2×HCID 67040752HCID 67040752, compound

Product 1

HCID 67040342HCID 67040342, compoundYield 44%

Procedure

The product of Example 107B was reacted with the product from Example 9B using the procedure from Example 95D substituting the product from Example 107B for the product from Example 95C and substituting the product from Example 9B for the product from Example 8E to provide the crude product was purified by HPLC with NH4OH to provide the title compound (28 mg, 44%). 1H NMR (300 MHz, DMSO-D6) δ ppm: 1.45 (s, 9 H), 2.66 (s, 3 H), 6.61 (d, J=8.09 Hz, 1 H), 7.04 (d, J=8.46 Hz, 1 H), 7.11-7.23 (m, 2 H), 7.25-7.39 (m, 3 H), 7.51 (d, J=8.46 Hz, 1 H), 7.71-7.80 (m, 1 H), 7.91 (dd, J=8.46, 2.21 Hz, 1 H), 8.09-8.12 (m, 1 H), 8.20 (d, J=1.84 Hz, 1 H), 8.60 (s, 1 H), 8.73 (d, J=8.46 Hz, 1 H), 9.44 (s, 1 H), 10.02 (s, 1 H), 10.36 (s, 1 H); MS (ESI+) m/z 641/643 (M+H)+.

Workup

  1. customto provide the crude product
  2. customwas purified by HPLC with NH4OH

Sources & evidence

ORD record
ord-d4767e49debf4a7181500f475bcf6c26
Source dataset
uspto-grants-2011_03
Patent number
US07910595B2

Reaction notes

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