Chloroform → (+)-2-Cyclopropylmethoxy-N-(7-[1,4]dioxan-2-yl-4-methoxy-benzothiazol-2-yl)-isonicotinamide

HRID 985848Notes

Reaction equation

HRID 985848 reaction equation
[H-].[Na+].Br[C:4]1[CH:5]=[C:6]([CH:27]=[CH:28][N:29]=1)[C:7]([NH:9][C:10]1[S:11][C:12]2[C:18]([CH:19]3[CH2:24][O:23][CH2:22][CH2:21][O:20]3)=[CH:17][CH:16]=[C:15]([O:25][CH3:26])[C:13]=2[N:14]=1)=[O:8].[OH:30][CH2:31][CH:32]1[CH2:34][CH2:33]1.C(Cl)(Cl)Cl>O1CCOCC1.CN(C=O)C>[CH:32]1([CH2:31][O:30][C:4]2[CH:5]=[C:6]([CH:27]=[CH:28][N:29]=2)[C:7]([NH:9][C:10]2[S:11][C:12]3[C:18]([CH:19]4[CH2:24][O:23][CH2:22][CH2:21][O:20]4)=[CH:17][CH:16]=[C:15]([O:25][CH3:26])[C:13]=3[N:14]=2)=[O:8])[CH2:34][CH2:33]1

Participants

6

Reactant 3

HCID 6212ChloroformHCID 75644CyclopropanemethanolHCID 23670120(+)-2-bromo-N-(7-[1,4]dioxan-2-yl-4-methoxy-benzothiazol-2-yl)-isonicotinamide sodium hydride

Product 1

HCID 22507765(+)-2-Cyclopropylmethoxy-N-(7-[1,4]dioxan-2-yl-4-methoxy-benzothiazol-2-yl)-isonicotinamide

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 312751,4-DioxaneSolvent

Procedure

From (+)-2-bromo-N-(7-[1,4]dioxan-2-yl-4-methoxy-benzothiazol-2-yl)-isonicotinamide sodium hydride and hydroxymethylcyclopropane in dioxane and DMF. [α]D20=+39.2° (c=1.02, CHCl3), ES-MS m/e (%): 442 (M+H+, 100).

Sources & evidence

ORD record
ord-8c8e7fb5b1af4e9aa545d293717e57df
Source dataset
uspto-grants-2005_03
Patent number
US06872833B2

Reaction notes

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