(2-Methoxypyridin-4-yl)boronic acid → 4-[5-(2-Methoxy-pyridin-4-yl)-[1,2,4]triazolo[1,5-a]pyrazin-8-ylamino]-N-pyridin-3-ylmethyl-benzamide

HRID 1784008Notes

Reaction equation

HRID 1784008 reaction equation
C[N:2]1CCN(C2C=CC(NC3C4N(N=CN=4)C(C4C=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.[CH3:59][O:60][C:61]1[CH:66]=[C:65](B(O)O)[CH:64]=[CH:63][N:62]=1>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].[CH3:59][O:60][C:61]1[CH:66]=[C:65]([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:64]=[CH:63][N:62]=1

Participants

8

Reactant 3

HCID 23546919(2-Methoxypyridin-4-yl)boronic acidHCID 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 575899504-[5-(2-Methoxy-pyridin-4-yl)-[1,2,4]triazolo[1,5-a]pyrazin-8-ylamino]-N-pyridin-3-ylmethyl-benzamideYield 73%

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 (120 mg, 0.28 mmol), 2-methoxypyridine-4-boronic acid (87 mg, 0.57 mmol) and Pd(PPh3)4 (81 mg, 0.07 mmol) in 1.5M K2CO3 (aq) (1.6 mL) and dioxane (2.9 mL). The crude material is purified by silica gel column chromatography eluting with DCM followed by 99:1 then 97:3 then 95:5 DCM:NH3 (7M in MeOH) to afford the title compound as a white solid (92.6 mg, 73%).

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-21b1c2adf0644a34b21ca76c607e94a5
Source dataset
uspto-grants-2009_03
Patent number
US07501411B2

Reaction notes

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