2-(But-3-en-1-yloxy)-5-fluorobenzylamine → Methyl(2S)-2-{5-[4-(but-3-en-1-yl)-4-methylpiperidin-1-yl]-2-({[2-(but-3-en-1-yloxy)-5-fluorophenyl]methyl}carbamoyl)-7-methylimidazo[1,2-a]pyridin-6-yl}-2-(tert-butoxy)acetate

Participants

Reaction Steps

Prepared from (S)-5-(4-(but-3-en-1-yl)-4-methylpiperidin-1-yl)-6-(1-(tert-butoxy)-2-methoxy-2-oxoethyl)-7-methylimidazo[1,2-a]pyridine-2-carboxylic acid sodium salt and 2-(but-3-en-1-yloxy)-5-fluorobenzylamine in 75% yield using the same procedure as (S)-methyl 2-(2-((2-(allyloxy)benzyl)carbamoyl)-5-(4-(but-3-en-1-yl)-4-methylpiperidin-1-yl)-7-methylimidazo[1,2-a]pyridin-6-yl)-2-(tert-butoxy)acetate. 1H NMR (500 MHz, CDCl3) [note: appears to be 2:1 mixture of rotamers, major rotamer transcribed] δ 8.24-8.21 (m, 1H), 7.90-7.81 (m, 1H), 7.23-7.18 (m, 1H), 7.14-7.09 (m, 1H), 6.95-6.87 (m, 1H), 6.83-6.77 (m, 1H), 6.12-6.08 (m, 1H), 6.05-5.89 (m, 2H), 5.28-5.21 (m, 1H), 5.19-5.15 (m, 1H), 5.14-4.98 (m, 2H), 4.69-4.64 (m, 2H), 4.07 (s, 2H), 3.74-3.73 (m, 1H), 3.71 (s, 3H), 3.64-3.49 (m, 1H), 3.14-2.93 (m, 1H), 2.91-2.83 (m, 1H), 2.70-2.60 (m, 2H), 2.47-2.46 (m, 3H), 2.17-2.09 (m, 2H), 1.71-1.60 (m, 6H), 1.26 (s, 9H), 1.15 (s, 3H); LCMS (ESI, M+1): 649.35.

Provenance & Evidence