Sodium borohydride → N-[2-(3-acetyl-5-amino-2-phenyl-2,3-dihydro-1,3,4-thiadiazol-2-yl)ethyl]methanesulfonamide

HRID 604576Notes

Reaction equation

[C:1]([N:4]1[C:8]([CH2:15][CH2:16][NH:17][S:18]([CH3:21])(=[O:20])=[O:19])([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[S:7][C:6]([NH:22]C(=O)C)=[N:5]1)(=[O:3])[CH3:2].[BH4-].[Na+].O.O.O.O.O.O.O.[Cl-].[Ce+3].[Cl-].[Cl-]>>[C:1]([N:4]1[N:5]=[C:6]([NH2:22])[S:7][C:8]1([CH2:15][CH2:16][NH:17][S:18]([CH3:21])(=[O:19])=[O:20])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)(=[O:3])[CH3:2]

Participants

Reactant 3

HCID 4311764Sodium borohydride

HCID 21585214Cerium trichloride heptahydrate

HCID 67039197N-[4-acetyl-5-(2-methanesulfonylaminoethyl)-5-phenyl-4,5-dihydro-1,3,4-thiadiazol-2-yl]acetamide

Product 1

HCID 67039184N-[2-(3-acetyl-5-amino-2-phenyl-2,3-dihydro-1,3,4-thiadiazol-2-yl)ethyl]methanesulfonamide

Procedure

In the same manner as that of the method described in WO2003/051854, from N-[4-acetyl-5-(2-methanesulfonylaminoethyl)-5-phenyl-4,5-dihydro-1,3,4-thiadiazol-2-yl]acetamide (5.22 g, 13.6 mmol) obtained in Step 2 mentioned above, sodium borohydride (5.14 g, 136 mmol), and cerium chloride heptahydrate (5.07 g, 13.6 mmol), N-[2-(3-acetyl-5-amino-2-phenyl-2,3-dihydro-1,3,4-thiadiazol-2-yl)ethyl]methane-sulfonamide was obtained.

Sources & evidence

ORD record: ord-58dffe6600de460ba3a1c02d953c43e3
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07910611B2

Reaction notes

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