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

HRID 985837Notes

Reaction equation

HRID 985837 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=O)=[C:5]([CH3:12])[CH:4]=1.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][C:3]([O:2][CH3:1])=[CH:4][C:5]=3[CH3:12])=[N:57][C:56]=2[C:55]([O:62][CH3:63])=[CH:54][CH:53]=1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 5972164-Methoxy-2-methylbenzoic 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 22507739(+)-N-(7-[1,4]Dioxan-2-yl-4-methoxy-benzothiazol-2-yl)-4-methoxy-2-methyl-benzamide

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8028TetrahydrofuranSolvent

Procedure

From 4-methoxy-2-methylbenzoic acid, HATU and N-ethyldiisopropylamine in THF, then treatment with (+)-7-[1,4]dioxan-2-yl-4-methoxy-benzothiazol-2-ylamine. [α]D20=+19.7° (c=0.62, CHCl3), ES-MS m/e (%): 415 (M+H+, 100).

Sources & evidence

ORD record
ord-fc785e2506a24e3f974d6d304a761823
Source dataset
uspto-grants-2005_03
Patent number
US06872833B2

Reaction notes

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