(3R,4S)-4-Aminotetrahydro-2H-pyran-3-ol → 4-[(6-chloropyridin-3-yl)methyl]-N-[(1S,2S)-2-hydroxycyclohexyl]-5,6,7,8-tetrahydroquinoline-2-carboxamide

HRID 2409510Notes

Reaction equation

HRID 2409510 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][C:9]2[C:18]3[CH2:17][CH2:16][CH2:15][CH2:14][C:13]=3[N:12]=[C:11]([C:19]([NH:21][C@@H:22]3[C@@H:27]([OH:28])[CH2:26]O[CH2:24][CH2:23]3)=[O:20])[CH:10]=2)=[CH:4][CH:3]=1.N[C@H:30]1CCOC[C@@H]1O>>[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][C:9]2[C:18]3[CH2:17][CH2:16][CH2:15][CH2:14][C:13]=3[N:12]=[C:11]([C:19]([NH:21][C@H:22]3[CH2:23][CH2:24][CH2:30][CH2:26][C@@H:27]3[OH:28])=[O:20])[CH:10]=2)=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 54180780(3R,4S)-4-Aminotetrahydro-2H-pyran-3-olHCID 547673451,5-anhydro-3-[({4-[(6-chloropyridin-3-yl)methyl]-5,6,7,8-tetrahydroquinolin-2-yl}carbonyl)amino]-2,3-dideoxy-L-threo-pentitol

Product 1

HCID 547673464-[(6-chloropyridin-3-yl)methyl]-N-[(1S,2S)-2-hydroxycyclohexyl]-5,6,7,8-tetrahydroquinoline-2-carboxamide

Procedure

4-[(6-Chloropyridin-3-yl)methyl]-N-[(1S,2S)-2-hydroxycyclohexyl]-5,6,7,8-tetrahydroquinoline-2-carboxamide was prepared by the procedure described for the synthesis of 1,5-anhydro-3-[({4-[(6-chloropyridin-3-yl)methyl]-5,6,7,8-tetrahydroquinolin-2-yl}carbonyl)amino]-2,3-dideoxy-L-threo-pentitol in Example 1, substituting (1S,2S)-2-aminocyclohexanol for (3R,4S)-4-aminotetrahydro-2H-pyran-3-ol.

Sources & evidence

ORD record
ord-8744e3e3a0ca4398975a1ab722b6e688
Source dataset
uspto-grants-2014_08
Patent number
US08815902B2

Reaction notes

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