Diisopropylethylamine → (+)-N-(7-[1,4]Dioxan-2-yl-4-methoxy-benzothiazol-2-yl)-2-(2-methoxy-ethoxymethyl)-isonicotinamide

HRID 985854Notes

Reaction equation

HRID 985854 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][C:7]1[CH:8]=[C:9]([CH:13]=[CH:14][N:15]=1)[C:10]([OH:12])=O.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(C(C)C)C(C)C)C.[O:49]1[CH2:54][CH2:53][O:52][CH2:51][CH:50]1[C:55]1[C:63]2[S:62][C:61]([NH2:64])=[N:60][C:59]=2[C:58]([O:65][CH3:66])=[CH:57][CH:56]=1>C1COCC1.C(Cl)(Cl)Cl>[O:49]1[CH2:54][CH2:53][O:52][CH2:51][CH:50]1[C:55]1[C:63]2[S:62][C:61]([NH:64][C:10](=[O:12])[C:9]3[CH:13]=[CH:14][N:15]=[C:7]([CH2:6][O:5][CH2:4][CH2:3][O:2][CH3:1])[CH:8]=3)=[N:60][C:59]=2[C:58]([O:65][CH3:66])=[CH:57][CH:56]=1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 225076892-(2-Methoxy-ethoxymethyl)-isonicotinic acidHCID 22507697(+)-7-[1,4)Dioxan-2-yl-4-methoxy-benzothiazol-2-ylamine

Product 1

HCID 22507714(+)-N-(7-[1,4]Dioxan-2-yl-4-methoxy-benzothiazol-2-yl)-2-(2-methoxy-ethoxymethyl)-isonicotinamide

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8028TetrahydrofuranSolvent

Procedure

From 2-(2-methoxy-ethoxymethyl)-isonicotinic acid, HATU and N-ethyldiisopropylamine in THF, then treatment with (+)-7-[1,4]dioxan-2-yl-4-methoxy-benzothiazol-2-ylamine. [α]D20=+69.2° (c=1.04, CHCl3), ES-MS m/e (%): 460 (M+H+, 100).

Sources & evidence

ORD record
ord-45a97203494d412cba70cb0a24a2eeb4
Source dataset
uspto-grants-2005_03
Patent number
US06872833B2

Reaction notes

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