Trifluoroacetic acid → 1-[(4S)-7-fluoro-3,4-dihydro-2H-chromen-4-yl]-3-[3-(2-methylpyridin-4-yl)-1H-pyrazolo[4,3-c]pyridin-6-yl]urea

HRID 571421Notes

Reaction equation

HRID 571421 reaction equation
[F:1][C:2]1[CH:11]=[C:10]2[C:5]([C@@H:6]([NH:12][C:13]([NH:15][C:16]3[N:21]=[CH:20][C:19]4[C:22]([C:44]5[CH:49]=[CH:48][N:47]=[C:46]([CH3:50])[CH:45]=5)=[N:23][N:24](C(C5C=CC=CC=5)(C5C=CC=CC=5)C5C=CC=CC=5)[C:18]=4[CH:17]=3)=[O:14])[CH2:7][CH2:8][O:9]2)=[CH:4][CH:3]=1.C(O)(C(F)(F)F)=O>>[F:1][C:2]1[CH:11]=[C:10]2[C:5]([C@@H:6]([NH:12][C:13]([NH:15][C:16]3[N:21]=[CH:20][C:19]4[C:22]([C:44]5[CH:49]=[CH:48][N:47]=[C:46]([CH3:50])[CH:45]=5)=[N:23][NH:24][C:18]=4[CH:17]=3)=[O:14])[CH2:7][CH2:8][O:9]2)=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 89525880(S)-1-(7-fluorochroman-4-yl)-3-(3-(2-methylpyridin-4-yl)-1-trityl-1H-pyrazolo[4,3-c]pyridin-6-yl)urea

Product 1

HCID 895259211-[(4S)-7-fluoro-3,4-dihydro-2H-chromen-4-yl]-3-[3-(2-methylpyridin-4-yl)-1H-pyrazolo[4,3-c]pyridin-6-yl]urea

Procedure

In a manner similar to that described in Scheme 6 and Example 30, (S)-1-(7-fluorochroman-4-yl)-3-(3-(2-methylpyridin-4-yl)-1-trityl-1H-pyrazolo[4,3-c]pyridin-6-yl)urea was deprotected with TFA to afford 1-[(4S)-7-fluoro-3,4-dihydro-2H-chromen-4-yl]-3-[3-(2-methylpyridin-4-yl)-1H-pyrazolo[4,3-c]pyridin-6-yl]urea. MS ESI calc'd. for C22H19FN6O2[M+1]+ 419, found 419.

Sources & evidence

ORD record
ord-f2d23c61fba64aff852557bd1fa649e7
Source dataset
uspto-grants-2015_05
Patent number
US09023865B2

Reaction notes

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