Potassium Phosphate, Tribasic → HCID 86639336, compound

HRID 1685349Notes

Reaction equation

HRID 1685349 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([NH:10][C:11]2[S:12][CH:13]=[C:14]([S:16][C:17]#N)[N:15]=2)=[N:8][CH:9]=1)([O-:3])=[O:2].SC[C@H]([C@@H](CS)O)O.ClC1[CH:33]=[CH:32][N:31]=[C:30]([C:34]([O:36][CH3:37])=[O:35])[CH:29]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>CN(C=O)C.CO>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([NH:10][C:11]2[S:12][CH:13]=[C:14]([S:16][C:17]3[CH:33]=[CH:32][N:31]=[C:30]([C:34]([O:36][CH3:37])=[O:35])[CH:29]=3)[N:15]=2)=[N:8][CH:9]=1)([O-:3])=[O:2]

Participants

7

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 446094D-1,4-DithiothreitolHCID 820890Methyl 4-ChloropicolinateHCID 86639337HCID 86639337, compound

Product 1

HCID 86639336HCID 86639336, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

Methanol (115 mL) was added to N-(5-nitropyridin-2-yl)-4-thiocyanatothiazol-2-amine (3.24 g, 11.6 mmol) and dithiothreitol (3.6 g, 23.3 mmol) at 23° C. Methyl 4-chloropicolinate (2.18 g, 12.8 mmol) was then added followed by potassium phosphate (3.27 g, 15.4 mmol) and DMF (115 mL). The reaction was stirred overnight, then poured into ice/water (1.5 L). The resulting precipitate was filtered on paper and dried under vacuum to give the title material (4.05 g, 90%). LC/MS (M+H)+: 390, (M−H)−: 388. HPLC ret. time (Condition E): 1.683 min.

Workup

  1. filtrationThe resulting precipitate was filtered on paper
  2. customdried under vacuum

Sources & evidence

ORD record
ord-678e432fe8484f859c1713d6acf0bb30
Source dataset
uspto-grants-2012_04
Patent number
US08148400B2

Reaction notes

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