3-(Pentafluorosulfanyl)benzoic acid → HCID 71667104, compound

HRID 1055768Notes

Reaction equation

HRID 1055768 reaction equation
CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH3:25][C:26]1[CH:32]=[CH:31][C:29]([NH2:30])=[CH:28][C:27]=1[N:33]1[C:40]2[N:36]([N:37]=[C:38]([C:41]3[S:45][CH:44]=[N:43][CH:42]=3)[CH:39]=2)[CH:35]=[CH:34]1.[F:46][S:47]([F:60])([F:59])([F:58])([F:57])[C:48]1[CH:49]=[C:50]([CH:54]=[CH:55][CH:56]=1)[C:51](O)=[O:52]>CN(C=O)C>[CH3:25][C:26]1[CH:32]=[CH:31][C:29]([NH:30][C:51](=[O:52])[C:50]2[CH:54]=[CH:55][CH:56]=[C:48]([S:47]([F:60])([F:46])([F:57])([F:58])[F:59])[CH:49]=2)=[CH:28][C:27]=1[N:33]1[C:40]2[N:36]([N:37]=[C:38]([C:41]3[S:45][CH:44]=[N:43][CH:42]=3)[CH:39]=2)[CH:35]=[CH:34]1

Participants

5

Reactant 3

HCID 27792093-(Pentafluorosulfanyl)benzoic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 89699621HCID 89699621, compound

Product 1

HCID 71667104HCID 71667104, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

193 mg (0.51 mmol) of HATU and 62 mg (0.51 mmol) of 4-N,N-dimethylaminopyridine (DMAP) were added to a solution of 100 mg (0.34 mmol) of the compound of Example 89A and 92 mg (0.37 mmol) of 3-(pentafluoro-λ6-sulphanyl)benzoic acid in 2 ml of DMF. The reaction was stirred at RT for 20 h. The reaction mixture was then purified directly by preparative HPLC (Method 16). This gave 50.2 mg (27% of theory) of the title compound.

Workup

  1. customThe reaction mixture was then purified directly by preparative HPLC (Method 16)

Sources & evidence

ORD record
ord-c9d910dea1594737b8df4721260c0de5
Source dataset
uspto-grants-2016_07
Patent number
US09394309B2

Reaction notes

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