Diisopropylethylamine → (+)-4-Dimethylamino-N-(7-[1,4]dioxan-2-yl-4-methoxy-benzothiazol-2-yl)-butyramide

HRID 985864Notes

Reaction equation

HRID 985864 reaction equation
Cl.[CH3:2][N:3]([CH3:10])[CH2:4][CH2:5][CH2:6][C:7](O)=[O:8].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:44]1[CH2:49][CH2:48][O:47][CH2:46][CH:45]1[C:50]1[C:58]2[S:57][C:56]([NH2:59])=[N:55][C:54]=2[C:53]([O:60][CH3:61])=[CH:52][CH:51]=1>C1COCC1.C(Cl)(Cl)Cl>[CH3:2][N:3]([CH3:10])[CH2:4][CH2:5][CH2:6][C:7]([NH:59][C:56]1[S:57][C:58]2[C:50]([CH:45]3[CH2:46][O:47][CH2:48][CH2:49][O:44]3)=[CH:51][CH:52]=[C:53]([O:60][CH3:61])[C:54]=2[N:55]=1)=[O:8]

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 126916404-(Dimethylamino)butyric acid hydrochlorideHCID 22507697(+)-7-[1,4)Dioxan-2-yl-4-methoxy-benzothiazol-2-ylamine

Product 1

HCID 22507699(+)-4-Dimethylamino-N-(7-[1,4]dioxan-2-yl-4-methoxy-benzothiazol-2-yl)-butyramide

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8028TetrahydrofuranSolvent

Procedure

From 4-(dimethylamino)butyric acid hydrochloride, HATU and N-ethyldiisopropylamine in THF, then treatment with (+)-7-[1,4]dioxan-2-yl-4-methoxy-benzothiazol-2-ylamine. [α]D20=+24.2° (c=0.53, CHCl3), ES-MS m/e (%): 380 (M+H+, 100).

Sources & evidence

ORD record
ord-f95767e42eda44cba0b26524ab4b2b4b
Source dataset
uspto-grants-2005_03
Patent number
US06872833B2

Reaction notes

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