Diethylamine → 2-Diethylaminomethyl-N-(7-methoxy-4-morpholin-4-yl-thiazolo[5,4-c]pyridin-2-yl)isonicotinamide

HRID 917447Notes

Reaction equation

HRID 917447 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].[CH2:30]([N:32](C(C)C)[CH:33](C)[CH3:34])[CH3:31].C(NCC)C>ClCCCl.C1COCC1.CN1C(=O)CCC1>[CH2:30]([N:32]([CH2:20][C:21]1[CH:22]=[C:23]([CH:27]=[CH:28][N:29]=1)[C:24]([NH:18][C:16]1[S:15][C:5]2[C:6]([N:9]3[CH2:10][CH2:11][O:12][CH2:13][CH2:14]3)=[N:7][CH:8]=[C:3]([O:2][CH3:1])[C:4]=2[N:17]=1)=[O:25])[CH2:33][CH3:34])[CH3:31]

Participants

8

Reactant 4

HCID 8021DiethylamineHCID 81531DiisopropylethylamineHCID 219192322-(Chloromethyl)pyridine-4-carbonyl chlorideHCID 860385537-Methoxy-4-morpholin-4-yl-thiazolo[5,4-c]pyridin-2-ylamine

Product 1

HCID 865972692-Diethylaminomethyl-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 diethylamine in NMP. ES-MS m/e (%): 457 (M+H+, 100).

Sources & evidence

ORD record
ord-304812c0ceb34198b3d310c42ef0a3a4
Source dataset
uspto-grants-2007_09
Patent number
US07273865B2

Reaction notes

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