4-Fluoroaniline → 5-Cyclopropyl-2-{4-[(4-fluorophenyl)amino]phenyl}-6-[(3-hydroxypropyl)(methylsulfonyl)amino]-N-methyl-2H-indazole-3-carboxamide

HRID 1037549Notes

Reaction equation

HRID 1037549 reaction equation
[CH:1]1([C:4]2[C:12]([N:13]([CH2:18][CH2:19][CH2:20][OH:21])[S:14]([CH3:17])(=[O:16])=[O:15])=[CH:11][C:10]3[C:6](=[C:7]([C:36]([NH:38][CH3:39])=[O:37])[N:8]([C:22]4[CH:27]=[CH:26][C:25]([NH:28]C5C=CC=CC=5F)=[CH:24][CH:23]=4)[N:9]=3)[CH:5]=2)[CH2:3][CH2:2]1.BrC1C=CC(N2C(C(NC)=O)=C3C(C=C(N(CCCO)S(C)(=O)=O)C(C4CC4)=C3)=N2)=CC=1.[F:72][C:73]1[CH:79]=[CH:78][C:76](N)=[CH:75][CH:74]=1>>[CH:1]1([C:4]2[C:12]([N:13]([CH2:18][CH2:19][CH2:20][OH:21])[S:14]([CH3:17])(=[O:15])=[O:16])=[CH:11][C:10]3[C:6](=[C:7]([C:36]([NH:38][CH3:39])=[O:37])[N:8]([C:22]4[CH:23]=[CH:24][C:25]([NH:28][C:76]5[CH:78]=[CH:79][C:73]([F:72])=[CH:74][CH:75]=5)=[CH:26][CH:27]=4)[N:9]=3)[CH:5]=2)[CH2:3][CH2:2]1

Participants

4

Reactant 3

HCID 97314-FluoroanilineHCID 569627692-(4-bromophenyl)-5-cyclopropyl-6-[3-hydroxypropyl(methylsulfonyl)amino]-N-methyl-indazole-3-carboxamideHCID 569627705-cyclopropyl-2-{4-[(2-fluorophenyl)amino]phenyl}-6-[(3-hydroxypropyl)(methylsulfonyl)amino]-N-methyl-2H-indazole-3-carboxamide

Product 1

HCID 675177915-Cyclopropyl-2-{4-[(4-fluorophenyl)amino]phenyl}-6-[(3-hydroxypropyl)(methylsulfonyl)amino]-N-methyl-2H-indazole-3-carboxamide

Procedure

5-Cyclopropyl-2-{4-[(4-fluorophenyl)amino]phenyl}-6-[(3-hydroxypropyl)(methylsulfonyl)amino]-N-methyl-2H-indazole-3-carboxamide (ii) was prepared similarly to Compound (5) (Method C, Step b) from 2-(4-bromophenyl)-5-cyclopropyl-6-[(3-hydroxypropyl)(methylsulfonyl)amino]-N-methyl-2H-indazole-3-carboxamide (i) using 4-fluoroaniline instead of 2-fluoroaniline.

Sources & evidence

ORD record
ord-c43dfc94bd3c4e7d9d2281cdc914ba96
Source dataset
uspto-grants-2013_10
Patent number
US08546389B2

Reaction notes

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