4-(1,1,1-Trifluoro-2-hydroxypropan-2-yl)benzoic acid → 4-(4-{5-Fluoro-2-methyl-3-[4-(2,2,2-trifluoro-1-hydroxy-1-methyl-ethyl)-benzoylamino]-phenyl}-7H-pyrrolo[2,3-d]pyrimidin-6-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid dimethylamide

HRID 589492Notes

Reaction equation

HRID 589492 reaction equation
CN(C)C(N1CC=C(C2NC3N=CN=C(C4C=CC=C(NC(=O)C5C=CC(C(O)(C)C)=CC=5F)C=4C(C4C=CC=CC=4)(C4C=CC=CC=4)O[SiH2]C(C)(C)C)C=3C=2)CC1)=O.[CH3:60][N:61]([CH3:88])[C:62]([N:64]1[CH2:69][CH:68]=[C:67]([C:70]2[NH:87][C:73]3[N:74]=[CH:75][N:76]=[C:77]([C:78]4[CH:83]=[C:82]([F:84])[CH:81]=[C:80]([NH2:85])[C:79]=4[CH3:86])[C:72]=3[CH:71]=2)[CH2:66][CH2:65]1)=[O:63].FC1C=C(C(O)(C)C)C=CC=1C(O)=O.[F:103][C:104]([F:118])([F:117])[C:105]([C:108]1[CH:116]=[CH:115][C:111]([C:112](O)=[O:113])=[CH:110][CH:109]=1)([OH:107])[CH3:106]>>[CH3:88][N:61]([CH3:60])[C:62]([N:64]1[CH2:65][CH:66]=[C:67]([C:70]2[NH:87][C:73]3[N:74]=[CH:75][N:76]=[C:77]([C:78]4[CH:83]=[C:82]([F:84])[CH:81]=[C:80]([NH:85][C:112](=[O:113])[C:111]5[CH:115]=[CH:116][C:108]([C:105]([OH:107])([CH3:106])[C:104]([F:103])([F:117])[F:118])=[CH:109][CH:110]=5)[C:79]=4[CH3:86])[C:72]=3[CH:71]=2)[CH2:68][CH2:69]1)=[O:63]

Participants

5

Reactant 4

HCID 578925274-(1,1,1-Trifluoro-2-hydroxypropan-2-yl)benzoic acidHCID 867309834-[4-(3-Amino-5-fluoro-2-methyl-phenyl)-7H-pyrrolo[2,3-d]pyrimidin-6-yl]-3,6-dihydro-2H-pyridine-1-carboxylic acid dimethylamideHCID 867309852-Fluoro-4-(2-hydroxypropan-2-yl)benzoic acidHCID 1317344644-(4-{2-(tert-Butyl-diphenyl-silanyloxymethyl)-3-[2-fluoro-4-(1-hydroxy-1-methyl-ethyl)-benzoylamino]-phenyl}-7H-pyrrolo[2,3-d]pyrimidin-6-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid dimethylamide

Product 1

HCID 712308514-(4-{5-Fluoro-2-methyl-3-[4-(2,2,2-trifluoro-1-hydroxy-1-methyl-ethyl)-benzoylamino]-phenyl}-7H-pyrrolo[2,3-d]pyrimidin-6-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid dimethylamide

Procedure

Example 18 was prepared analogue to Intermediate 9 by replacing Intermediate 7 with Intermediate 6 and Intermediate 8 with 4-(2,2,2-trifluoro-1-hydroxy-1-methyl-ethyl)-benzoic acid (WO2007/145834).

Sources & evidence

ORD record
ord-ad6c307408af4896b0af5963fc29ca6e
Source dataset
uspto-grants-2016_01
Patent number
US09233111B2

Reaction notes

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