2-Amino-5-methylpyridine → HCID 59560382, compound

HRID 1177314Notes

Reaction equation

HRID 1177314 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][N:3]=1.[CH:9]([O:12][C:13]1[CH:14]=[C:15]2[O:19][CH:18]=[CH:17][C:16]2=[C:20]([C:22](OC)=[O:23])[CH:21]=1)([CH3:11])[CH3:10]>>[CH:9]([O:12][C:13]1[CH:14]=[C:15]2[O:19][CH:18]=[CH:17][C:16]2=[C:20]([C:22]([NH:1][C:2]2[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][N:3]=2)=[O:23])[CH:21]=1)([CH3:11])[CH3:10]

Participants

3

Reactant 2

HCID 153482-Amino-5-methylpyridineHCID 59560409HCID 59560409, compound

Product 1

HCID 59560382HCID 59560382, compound

Procedure

The title compound was prepared in a similar manner as described for Example 1, from 2-amino-5-methyl pyridine and methyl 6-isopropoxybenzofuran-4-carboxylate (344a) to give a white solid (28 mg, 37% yield). 1H NMR (400 MHz, CDCl3) δ 8.77 (s, 1 H) 8.29 (d, J=8.56 Hz, 1 H) 8.04 (d, J=2.52 Hz, 1 H) 7.65 (d, J=2.27 Hz, 1 H) 7.58 (dd, J=8.31, 2.27 Hz, 1 H) 7.34 (d, J=2.01 Hz, 1 H) 7.21-7.23 (m, 2 H) 4.55-4.64 (m, 1 H) 2.30 (s, 3 H) 1.37 (d, J=6.04 Hz, 6 H); LCMS for C18H18N2O3 m/z 311.10 (M+H)+.

Sources & evidence

ORD record
ord-97c60548005d4c419c52da32555c998c
Source dataset
uspto-grants-2010_11
Patent number
US07842713B2

Reaction notes

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