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 605988Notes

Reaction equation

HRID 605988 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-4d5869e613af439ba27b83f68dbb80d9
Source dataset
uspto-grants-2011_03
Patent number
US07915256B2

Reaction notes

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