4-(Pentafluoro-lambda6-sulfanyl)benzoic acid → 4-(4-{5-Fluoro-2-methyl-3-[4-(pentafluoro-sulfanyl)-benzoylamino]-phenyl}-7H-pyrrolo[2,3-d]pyrimidin-6-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester

HRID 589504Notes

Reaction equation

HRID 589504 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.[C:60]([O:64][C:65]([N:67]1[CH2:72][CH:71]=[C:70]([C:73]2[NH:90][C:76]3[N:77]=[CH:78][N:79]=[C:80]([C:81]4[CH:86]=[C:85]([F:87])[CH:84]=[C:83]([NH2:88])[C:82]=4[CH3:89])[C:75]=3[CH:74]=2)[CH2:69][CH2:68]1)=[O:66])([CH3:63])([CH3:62])[CH3:61].FC1C=C(C(O)(C)C)C=CC=1C(O)=O.[F:105][S:106]([F:119])([F:118])([F:117])([F:116])[C:107]1[CH:115]=[CH:114][C:110]([C:111](O)=[O:112])=[CH:109][CH:108]=1>>[C:60]([O:64][C:65]([N:67]1[CH2:68][CH:69]=[C:70]([C:73]2[NH:90][C:76]3[N:77]=[CH:78][N:79]=[C:80]([C:81]4[CH:86]=[C:85]([F:87])[CH:84]=[C:83]([NH:88][C:111](=[O:112])[C:110]5[CH:114]=[CH:115][C:107]([S:106]([F:119])([F:105])([F:116])([F:117])[F:118])=[CH:108][CH:109]=5)[C:82]=4[CH3:89])[C:75]=3[CH:74]=2)[CH2:71][CH2:72]1)=[O:66])([CH3:63])([CH3:62])[CH3:61]

Participants

5

Reactant 4

HCID 27792104-(Pentafluoro-lambda6-sulfanyl)benzoic acidHCID 867309852-Fluoro-4-(2-hydroxypropan-2-yl)benzoic acidHCID 867309964-[4-(3-Amino-5-fluoro-2-methyl-phenyl)-7H-pyrrolo[2,3-d]pyrimidin-6-yl]-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl esterHCID 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 867309974-(4-{5-Fluoro-2-methyl-3-[4-(pentafluoro-sulfanyl)-benzoylamino]-phenyl}-7H-pyrrolo[2,3-d]pyrimidin-6-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester

Procedure

Intermediate 23 was prepared analogue to Intermediate 9 by replacing Intermediate 7 with Intermediate 20 and Intermediate 8 with 4-(pentafluoro-sulfanyl)-benzoic acid.

Sources & evidence

ORD record
ord-64d5692cdf0841149807476512946d75
Source dataset
uspto-grants-2016_01
Patent number
US09233111B2

Reaction notes

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