4-Ethylpyridin-2-amine → HCID 58869959, compound

HRID 1191710Notes

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]1[CH:39]=C(CC)C=CN=1>>[CH2:34]([C:9]1[CH:4]=[CH:5][N:6]=[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)[CH:8]=1)[CH3:39]

Participants

Reactant 2

HCID 1184254-Ethylpyridin-2-amine

HCID 16058694HCID 16058694, compound

Product 1

HCID 58869959HCID 58869959, compound

Procedure

The product from Example 1, Part C (0.3 g, 0.93 mmol) and 2-amino-4-ethylpyridine (0.171 g, 1.4 mmol) were converted to the title compound by the method described in Part B of Example 16 (121 mg, 30%). 1H NMR (300 MHz, CDCl3) δ 8.53 (broad s, 1H); 8.15 (d, J=5.16 Hz, 1H); 7.99 (s, 1H); 7.23 (d, J=8.4 Hz, 2H); 6.92 (m, 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); 3.77 (s, 3H); 2.90 (s, 2H); 2.67 (q, J=7.4 Hz, 2H); 1.95 (s, 3H); 1.84 (s, 3H); 1.27 (t, J=7.6 Hz, 3H). MS: m/z (MH+) 426.

Sources & evidence

ORD record: ord-2d859c66c0944676a6665796213e83c5
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08680122B2

Reaction notes

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