Trifluoroacetic acid → (R)-1-(3-(2,2-difluoro-1-methylcyclopropyl)-1H-pyrazolo[4,3-c]pyridin-6-yl)-3-(1-(4-fluorophenyl)ethyl)urea 2,2,2-trifluoroacetate

HRID 571410Notes

Reaction equation

HRID 571410 reaction equation
Cl[C:2]1[N:7]=[CH:6][C:5]2[C:8]([C:30]3([CH3:35])[CH2:32][C:31]3([F:34])[F:33])=[N:9][N:10](C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[C:4]=2[CH:3]=1.[F:36][C:37]1[CH:42]=[CH:41][C:40]([C@H:43]([NH:45][C:46]([NH2:48])=[O:47])[CH3:44])=[CH:39][CH:38]=1.[C:49]([OH:55])([C:51]([F:54])([F:53])[F:52])=[O:50]>>[F:52][C:51]([F:54])([F:53])[C:49]([OH:55])=[O:50].[F:34][C:31]1([F:33])[CH2:32][C:30]1([C:8]1[C:5]2[CH:6]=[N:7][C:2]([NH:48][C:46]([NH:45][C@@H:43]([C:40]3[CH:39]=[CH:38][C:37]([F:36])=[CH:42][CH:41]=3)[CH3:44])=[O:47])=[CH:3][C:4]=2[NH:10][N:9]=1)[CH3:35]

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 1176008406-chloro-3-(2,2-difluoro-1-methylcyclopropyl)-1-trityl-1H-pyrazolo[4,3-c]pyridineHCID 117601722(R)-1-(1-(4-fluorophenyl)ethyl)urea

Product 1

HCID 178462160(R)-1-(3-(2,2-difluoro-1-methylcyclopropyl)-1H-pyrazolo[4,3-c]pyridin-6-yl)-3-(1-(4-fluorophenyl)ethyl)urea 2,2,2-trifluoroacetate

Procedure

In a manner similar to that described in Scheme 6 and Example 30, 6-chloro-3-(2,2-difluoro-1-methylcyclopropyl)-1-trityl-1H-pyrazolo[4,3-c]pyridine was reacted with (R)-1-(1-(4-fluorophenyl)ethyl)urea (Xantphos, Pd(OAc)2, Cs2CO3, dioxane, 80° C., overnight) and then deprotected with TFA to provide (R)-1-(3-(2,2-difluoro-1-methylcyclopropyl)-1H-pyrazolo[4,3-c]pyridin-6-yl)-3-(1-(4-fluorophenyl)ethyl)urea 2,2,2-trifluoroacetate. MS ESI calc'd. for C19H18F3N5O[M+1]+ 390, found 390.

Sources & evidence

ORD record
ord-e8b5ab63699c42de978f091a291e604a
Source dataset
uspto-grants-2015_05
Patent number
US09023865B2

Reaction notes

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