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

HRID 985836Notes

Reaction equation

HRID 985836 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][N:12]=1)[C:7]([OH:9])=O)[CH3:2].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:46]1[CH2:51][CH2:50][O:49][CH2:48][CH:47]1[C:52]1[C:60]2[S:59][C:58]([NH2:61])=[N:57][C:56]=2[C:55]([O:62][CH3:63])=[CH:54][CH:53]=1>C1COCC1.C(Cl)(Cl)Cl>[O:46]1[CH2:51][CH2:50][O:49][CH2:48][CH:47]1[C:52]1[C:60]2[S:59][C:58]([NH:61][C:7](=[O:9])[C:6]3[CH:10]=[CH:11][N:12]=[C:4]([O:3][CH2:1][CH3:2])[CH:5]=3)=[N:57][C:56]=2[C:55]([O:62][CH3:63])=[CH:54][CH:53]=1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 5924012-Ethoxyisonicotinic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 22507697(+)-7-[1,4)Dioxan-2-yl-4-methoxy-benzothiazol-2-ylamine

Product 1

HCID 22507722(+)-N-(7-[1,4]Dioxan-2-yl-4-methoxy-benzothiazol-2-yl)-2-ethoxy-isonicotinamide

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8028TetrahydrofuranSolvent

Procedure

From 2-ethoxy-isonicotinic acid, HATU and N-ethyldiisopropylamine in THF, then treatment with (+)-7-[1,4]dioxan-2-yl-4-methoxy-benzothiazol-2-ylamine. [α]D20=+31.7° (c=0.61, CHCl3), ES-MS m/e (%): 416 (M+H+, 100).

Sources & evidence

ORD record
ord-18f5c203b3894340b439b15d25a5da1e
Source dataset
uspto-grants-2005_03
Patent number
US06872833B2

Reaction notes

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