Piperidin-4-ol → 2-(4-Hydroxy-piperidin-1-ylmethyl)-N-(7-methoxy-4-morpholin-4-yl-thiazolo[5,4-c]pyridin-2-yl)-isonicotinamide

HRID 917448Notes

Reaction equation

HRID 917448 reaction equation
[CH3:1][O:2][C:3]1[C:4]2[N:17]=[C:16]([NH2:18])[S:15][C:5]=2[C:6]([N:9]2[CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)=[N:7][CH:8]=1.Cl[CH2:20][C:21]1[CH:22]=[C:23]([CH:27]=[CH:28][N:29]=1)[C:24](Cl)=[O:25].C(N(C(C)C)C(C)C)C.[OH:39][CH:40]1[CH2:45][CH2:44][NH:43][CH2:42][CH2:41]1>ClCCCl.C1COCC1.CN1C(=O)CCC1>[OH:39][CH:40]1[CH2:45][CH2:44][N:43]([CH2:20][C:21]2[CH:22]=[C:23]([CH:27]=[CH:28][N:29]=2)[C:24]([NH:18][C:16]2[S:15][C:5]3[C:6]([N:9]4[CH2:10][CH2:11][O:12][CH2:13][CH2:14]4)=[N:7][CH:8]=[C:3]([O:2][CH3:1])[C:4]=3[N:17]=2)=[O:25])[CH2:42][CH2:41]1

Participants

8

Reactant 4

HCID 79341Piperidin-4-olHCID 81531DiisopropylethylamineHCID 219192322-(Chloromethyl)pyridine-4-carbonyl chlorideHCID 860385537-Methoxy-4-morpholin-4-yl-thiazolo[5,4-c]pyridin-2-ylamine

Product 1

HCID 865972702-(4-Hydroxy-piperidin-1-ylmethyl)-N-(7-methoxy-4-morpholin-4-yl-thiazolo[5,4-c]pyridin-2-yl)-isonicotinamide

Reagents, catalysts & solvents 3

HCID 111,2-DichloroethaneSolventHCID 8028TetrahydrofuranSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

From 7-methoxy-4-morpholin-4-yl-thiazolo[5,4-c]pyridin-2-ylamine with 2-chloromethyl-isonicotinoyl chloride and N-ethyldiisopropylamine in 1,2-dichloroethane and THF; then subsequent treatment with 4-hydroxypiperidine in NMP. ES-MS m/e (%): 485 (M+H+, 100).

Sources & evidence

ORD record
ord-911660bfa8be484db32efec264527cbf
Source dataset
uspto-grants-2007_09
Patent number
US07273865B2

Reaction notes

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