2-Amino-4-methylpyridine → HCID 58869955, compound

HRID 1191709Notes

Reaction equation

HRID 1191709 reaction equation
COC(=O)[C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11](=[O:31])[CH2:12][S:13][CH:14]2[C:18]([CH3:19])=[C:17]([CH3:20])[C:16](=[O:21])[N:15]2[CH2:22][C:23]2[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=2)=[N:6][CH:5]=1.N[C:34]1C=C(C)C=CN=1>>[CH3:30][O:29][C:26]1[CH:25]=[CH:24][C:23]([CH2:22][N:15]2[C:16](=[O:21])[C:17]([CH3:20])=[C:18]([CH3:19])[CH:14]2[S:13][CH2:12][C:11]([NH:10][C:7]2[CH:8]=[C:9]([CH3:34])[CH:4]=[CH:5][N:6]=2)=[O:31])=[CH:28][CH:27]=1

Participants

3

Reactant 2

HCID 15332-Amino-4-methylpyridineHCID 16058694HCID 16058694, compound

Product 1

HCID 58869955HCID 58869955, compound

Procedure

The product from Example 1, Part C (0.3 g, 0.93 mmol) and 2-amino-4-picoline (0.151 g, 1.4 mmol) were converted to the title compound by the method described in Part B of Example 16 (0.223 g, 58%). 1H NMR (300 MHz, CDCl3) δ 8.28 (broad s, 1H); 7.92 (d, J=8 Hz, 1H), 7.60 (t, J=7.8 Hz, 1H); 7.23 (d, J=8.6 Hz, 2H); 6.88 (d, J=7.4 Hz, 1H); 6.84 (d, J=8.5 Hz, 2H); 5.11 (d, J=15 Hz, 1H), 4.61 (s, 1H); 4.16 (d, 15 Hz, 1H); 3.76 (s, 3H); 2.89 (s, 2H); 2.44 (s, 3H); 1.94 (s, 3H); 1.84 (s, 3H). MS: m/z (MH+) 412.

Sources & evidence

ORD record
ord-3e0dfb7be61b4ac195ab0c7927b0eb7c
Source dataset
uspto-grants-2014_03
Patent number
US08680122B2

Reaction notes

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