1,3,4-Thiadiazol-2-amine → HCID 57788027, compound

HRID 249953Notes

Reaction equation

HRID 249953 reaction equation
C([C:3]1[CH:8]=[C:7]([O:9][CH3:10])[C:6]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][C:16]([S:19]([CH3:27])(=[N:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])=[O:20])=[CH:15][CH:14]=2)=[CH:5][C:4]=1[N:28]=[CH:29][N:30]([CH3:32])C)#N.[NH2:33][C:34]1[S:35][CH:36]=[N:37][N:38]=1.ClCCl.CO>CO>[CH2:25]([O:24][C:22]([N:21]=[S:19]([CH3:27])([C:16]1[CH:15]=[CH:14][C:13]([CH2:12][O:11][C:6]2[CH:5]=[C:4]3[C:3]([C:32]([NH:33][C:34]4[S:35][CH:36]=[N:37][N:38]=4)=[N:30][CH:29]=[N:28]3)=[CH:8][C:7]=2[O:9][CH3:10])=[CH:18][CH:17]=1)=[O:20])=[O:23])[CH3:26]

Participants

5

Reactant 3

HCID 199091,3,4-Thiadiazol-2-amineHCID 21226129Dichloromethane methanolHCID 57788010HCID 57788010, compound

Product 1

HCID 57788027HCID 57788027, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

According to GWP 5, the reaction of N′-(2-cyano-5-{4-[(RS)-N-(ethoxycarbonyl)-S-methylsulphonimidoyl]benzyloxy}-4-methoxyphenyl)-N,N-dimethylformimidamide (85 mg, 0.19 mmol) with 2-amino-1,3,4-thiadiazole (23 mg, 0.22 mmol) and chromatographic purification (silica gel, dichloromethane/methanol: 0→30% methanol) gives the desired product in 40% yield (38 mg).

Sources & evidence

ORD record
ord-46d1cb3e1a72422299107c3e0fa56beb
Source dataset
uspto-grants-2011_01
Patent number
US07863283B2

Reaction notes

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