Trifluoroacetic acid → N-[2,4-difluoro-3-(4-methoxy-7H-pyrrolo[2,3-d]pyrimidin-5-ylmethyl)-phenyl]-benzenesulfonamide
Reaction equation
[CH3:1][O:2][C:3]1[C:4]2[CH:11]=[CH:10][NH:9][C:5]=2[N:6]=[CH:7][N:8]=1.FC1C(C=O)=C(F)C=CC=1NS(CCC)(=O)=O.[F:29][C:30]1[C:35]([CH:36]=O)=[C:34]([F:38])[CH:33]=[CH:32][C:31]=1[NH:39][S:40]([C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)(=[O:42])=[O:41].C(OC1C2C=CNC=2N=CN=1)C.C([SiH](CC)CC)C.FC(F)(F)C(O)=O>>[F:29][C:30]1[C:35]([CH2:36][C:11]2[C:4]3[C:3]([O:2][CH3:1])=[N:8][CH:7]=[N:6][C:5]=3[NH:9][CH:10]=2)=[C:34]([F:38])[CH:33]=[CH:32][C:31]=1[NH:39][S:40]([C:43]1[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=1)(=[O:42])=[O:41]Participants
7
Reactant 6
Product 1
Procedure
were prepared similarly to the protocol of Scheme 7, steps 2 and 3, replacing 4-methyl-7H-pyrrolo[2,3-d]pyrimidine 42 with 4-methoxy-7H-pyrrolo[2,3-d]pyrimidine 3 and propane-1-sulfonic acid (2,4-difluoro-3-formyl-phenyl)-amide 9 with N-(2,4-Difluoro-3-formyl-phenyl)-benzenesulfonamide in step 2 for P-0072 and replacing 4-methyl-7H-pyrrolo[2,3-d]pyrimidine 42 with 4-ethoxy-7H-pyrrolo[2,3-d]pyrimidine 47 in step 2 for P-0075. Alternatively, the intermediate in the reaction to form P-0072 was reduced using triethylsilane and trifluoroacetic acid to form N-[2,4-difluoro-3-(4-methoxy-7H-pyrrolo[2,3-d]pyrimidin-5-ylmethyl)-phenyl]-benzenesulfonamide P-0073
Workup
- customwere prepared similarly to the protocol of Scheme 7, steps 2 and 3
- customAlternatively, the intermediate in the reaction
- customto form P-0072
Sources & evidence
- ORD record
- ord-f9b3f73f46f04915a7162a50a84c68d3
- Source dataset
- uspto-grants-2012_04
- Patent number
- US08153641B2
Reaction notes
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