Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) → 7-Fluoro-9-oxo-9H-xanthene-3-carboxylic acid diethylamide

HRID 733402Notes

Reaction equation

HRID 733402 reaction equation
[F:1][C:2]1[CH:15]=[C:14]2[C:5]([O:6][C:7]3[CH:8]=[C:9]([C:17]([OH:19])=O)[CH:10]=[CH:11][C:12]=3[C:13]2=[O:16])=[CH:4][CH:3]=1.COC1C=CC=C2C=1OC1C=C(C(O)=O)C=CC=1C2=O.BrC1C=CC=C2C=1OC1C=C(C(O)=O)C=CC=1C2=O.CN(C(ON1N=N[C:69]2C=[CH:71][CH:72]=[N:73][C:68]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>>[CH2:72]([N:73]([CH2:68][CH3:69])[C:17]([C:9]1[CH:10]=[CH:11][C:12]2[C:13](=[O:16])[C:14]3[C:5]([O:6][C:7]=2[CH:8]=1)=[CH:4][CH:3]=[C:2]([F:1])[CH:15]=3)=[O:19])[CH3:71]

Participants

6

Reactant 5

HCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 574366735-methoxy-9-oxo-9H-xanthene-3-carboxylic acidHCID 578392377-Fluoro-9-oxo-9H-xanthene-3-carboxylic acidHCID 578392455-Bromo-9-oxo-9H-xanthene-3-carboxylic acid

Product 1

HCID 578392357-Fluoro-9-oxo-9H-xanthene-3-carboxylic acid diethylamide

Procedure

Using an adaptation of the method described in Procedure 16, substituting 7-fluoro-9-oxo-9H-xanthene-3-carboxylic acid, 3e for 5-methoxy-9-oxo-9H-xanthene-3-carboxylic acid, 3d, and HATU for HBTU, the title compound 7-fluoro-9-oxo-9H-xanthene-3-carboxylic acid diethylamide, 4e was obtained. MS m/z (MH+) 314.

Sources & evidence

ORD record
ord-c591f457086b4971a3173f7488ad8725
Source dataset
uspto-grants-2009_09
Patent number
US07589104B2

Reaction notes

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