4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole → 4-(5-(1H-Pyrazol-4-yl)-[1,2,4]triazolo[1,5-a]pyrazin-8-ylamino)-N-(pyridin-3-ylmethyl)benzamide

HRID 1784007Notes

Reaction equation

HRID 1784007 reaction equation
C[N:2]1CCN(C2C=CC(NC3C4[N:17]([N:29]=[CH:30]N=4)[C:18]([C:21]4C=C(C(N)=O)SC=4)=CN=3)=CC=2)CC1.Br[C:33]1[N:38]2[N:39]=[CH:40][N:41]=[C:37]2[C:36]([NH:42][C:43]2[CH:58]=[CH:57][C:46]([C:47]([NH:49][CH2:50][C:51]3[CH:52]=[N:53][CH:54]=[CH:55][CH:56]=3)=[O:48])=[CH:45][CH:44]=2)=[N:35][CH:34]=1.CC1(C)C(C)(C)OB(C2C=NNC=2)O1>C([O-])([O-])=O.[K+].[K+].O1CCOCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[NH3:2].[NH:17]1[CH:18]=[C:21]([C:33]2[N:38]3[N:39]=[CH:40][N:41]=[C:37]3[C:36]([NH:42][C:43]3[CH:58]=[CH:57][C:46]([C:47]([NH:49][CH2:50][C:51]4[CH:52]=[N:53][CH:54]=[CH:55][CH:56]=4)=[O:48])=[CH:45][CH:44]=3)=[N:35][CH:34]=2)[CH:30]=[N:29]1

Participants

8

Reactant 3

HCID 27740104-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 575899284-{8-[4-(4-Methyl-piperazin-1-yl)-phenylamino]-[1,2,4]triazolo[1,5-a]pyrazin-5-yl}-thiophene-2-carboxylic acid amideHCID 575899444-(5-Bromo-[1,2,4]triazolo[1,5-a]pyrazin-8-ylamino)-N-pyridin-3-ylmethyl-benzamide

Product 2

HCID 222AmmoniaHCID 1359796394-(5-(1H-Pyrazol-4-yl)-[1,2,4]triazolo[1,5-a]pyrazin-8-ylamino)-N-(pyridin-3-ylmethyl)benzamideYield 20%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 11430Potassium CarbonateSolventHCID 312751,4-DioxaneSolvent

Procedure

This compound may be prepared using methods as described for Compound 6, step 4 using 4-(5-bromo-[1,2,4]triazolo[1,5-a]pyrazin-8-ylamino)-N-pyridin-3-ylmethyl-benzamide (100 mg, 0.24 mmol), 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrazole (93 mg, 0.48 mmol) and Pd(PPh3)4 (70 mg, 0.06 mmol) in 1.5M K2CO3 (aq) (1.4 mL) and dioxane (2.5 mL). The crude material is purified by silica gel column chromatography eluting with DCM followed by 98:2 then 96:4 then 90:10 DCM:NH3 (7M in MeOH) to afford the title compound as a white solid (19.6 mg, 20%).

Workup

  1. customThis compound may be prepared
  2. customThe crude material is purified by silica gel column chromatography
  3. washeluting with DCM

Sources & evidence

ORD record
ord-f373c043f7f84a34a628cd9ded59a339
Source dataset
uspto-grants-2009_03
Patent number
US07501411B2

Reaction notes

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