(S)-tert-butyl 1-(5-aminopyridin-2-yl)piperidin-3-ylcarbamate → (S)-tert-butyl (1-(5-((6-chloro-3-propionyl-1,5-naphthyridin-4-yl)amino)pyridin-2-yl)piperidin-3-yl)carbamate

HRID 2178965Notes

Reaction equation

HRID 2178965 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([Cl:12])[N:10]=2)[N:5]=[CH:4][C:3]=1[C:13](=[O:16])[CH2:14][CH3:15].[NH2:17][C:18]1[CH:19]=[CH:20][C:21]([N:24]2[CH2:29][CH2:28][CH2:27][C@H:26]([NH:30][C:31](=[O:37])[O:32][C:33]([CH3:36])([CH3:35])[CH3:34])[CH2:25]2)=[N:22][CH:23]=1>>[C:33]([O:32][C:31](=[O:37])[NH:30][C@H:26]1[CH2:27][CH2:28][CH2:29][N:24]([C:21]2[CH:20]=[CH:19][C:18]([NH:17][C:2]3[C:11]4[C:6](=[CH:7][CH:8]=[C:9]([Cl:12])[N:10]=4)[N:5]=[CH:4][C:3]=3[C:13](=[O:16])[CH2:14][CH3:15])=[CH:23][N:22]=2)[CH2:25]1)([CH3:36])([CH3:34])[CH3:35]

Participants

3

Reactant 2

HCID 66715841(S)-tert-butyl 1-(5-aminopyridin-2-yl)piperidin-3-ylcarbamateHCID 897056421-(4,6-Dichloro-1,5-naphthyridin-3-yl)propan-1-one

Product 1

HCID 117798301(S)-tert-butyl (1-(5-((6-chloro-3-propionyl-1,5-naphthyridin-4-yl)amino)pyridin-2-yl)piperidin-3-yl)carbamateYield 109.8%

Procedure

Following general procedure I, 1-(4,6-dichloro-1,5-naphthyridin-3-yl)propan-1-one (250 mg, 0.98 mmol) was reacted with (S)-tert-butyl 1-(5-aminopyridin-2-yl)piperidin-3-ylcarbamate (430 mg, 1.5 mmol) to afford the desired product (550 mg, crude) as an dark brown solid: 1H NMR (500 MHz, CDCl3) δ 11.29 (s, 1H), 9.03 (s, 1H), 8.11 (d, J=9.0 Hz, 1H), 8.01 (d, J=3.0 Hz, 1H), 7.47 (d, J=9.0 Hz, 1H), 7.31-7.29 (m, 1H), 6.72 (d, J=9.0 Hz, 1H), 4.79 (br s, 1H), 3.90-3.61 (m, 4H), 3.51-3.25 (m, 2H), 3.07 (q, J=7.0 Hz, 2H), 1.96-1.84 (m, 1H), 1.82-1.70 (m, 1H), 1.72-1.55 (m, 1H), 1.45 (s, 9H), 1.26 (t, J=7.0 Hz, 3H); ESI MS m/z 511 [M+H]+

Sources & evidence

ORD record
ord-6a17ae61a0994c7984e521876addd8f4
Source dataset
uspto-grants-2015_06
Patent number
US09067937B2

Reaction notes

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