Methoxyacetic Acid → (+)-N-(7-[1,4]Dioxan-2-yl-4-methoxy-benzothiazol-2-yl)-2-methoxy-acetamide

HRID 985844Notes

Reaction equation

HRID 985844 reaction equation
[CH3:1][O:2][CH2:3][C:4]([OH:6])=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:40]1[CH2:45][CH2:44][O:43][CH2:42][CH:41]1[C:46]1[C:54]2[S:53][C:52]([NH2:55])=[N:51][C:50]=2[C:49]([O:56][CH3:57])=[CH:48][CH:47]=1>C1COCC1.C(Cl)(Cl)Cl>[O:40]1[CH2:45][CH2:44][O:43][CH2:42][CH:41]1[C:46]1[C:54]2[S:53][C:52]([NH:55][C:4](=[O:6])[CH2:3][O:2][CH3:1])=[N:51][C:50]=2[C:49]([O:56][CH3:57])=[CH:48][CH:47]=1

Participants

7

Reactant 4

HCID 12251Methoxyacetic AcidHCID 81531DiisopropylethylamineHCID 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 22507688(+)-N-(7-[1,4]Dioxan-2-yl-4-methoxy-benzothiazol-2-yl)-2-methoxy-acetamide

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8028TetrahydrofuranSolvent

Procedure

From methoxyacetic acid, HATU and N-ethyldiisopropylamine in THF, then treatment with (+)-7-[1,4]dioxan-2-yl-4-methoxy-benzothiazol-2-ylamine. [α]D20=+24.9° (c=1.05, CHCl3), ES-MS m/e (%): 339 (M+H+, 100).

Sources & evidence

ORD record
ord-290dcd50563b45209c197a0fe04a3f6e
Source dataset
uspto-grants-2005_03
Patent number
US06872833B2

Reaction notes

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