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

HRID 605908

反応式

HRID 605908 の反応式
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:44]=[CH:45][C:46]([N:52]3[CH2:57][CH2:56][O:55][CH2:54][CH2:53]3)=[C:47]([CH:51]=2)[C:48]([NH2:50])=[O:49])=[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:44]=[CH:45][C:46]([N:52]4[CH2:53][CH2:54][O:55][CH2:56][CH2:57]4)=[C:47]([CH:51]=3)[C:48]([NH2:50])=[O:49])=[N:35][CH:34]=2)[CH:30]=[N:29]1

参加物

8

反応物 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 575900535-(5-Bromo-[1,2,4]triazolo[1,5-a]pyrazin-8-ylamino)-2-morpholin-4-yl-benzamide

生成物 2

HCID 222AmmoniaHCID 1359796085-(5-(1H-Pyrazol-4-yl)-[1,2,4]triazolo[1,5-a]pyrazin-8-ylamino)-2-morpholinobenzamide収率 30%

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 11430Potassium Carbonate溶媒HCID 312751,4-Dioxane溶媒

実験手順

This compound may be prepared using methods as described for Compound 6, step 4 using 5-(5-bromo-[1,2,4]triazolo[1,5-a]pyrazin-8-ylamino)-2-morpholin-4-yl-benzamide (140 mg, 0.33 mmol), 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrazole (130 mg, 0.67 mmol) and Pd(PPh3)4 (96 mg, 0.083 mmol) in 1.5M K2CO3 (aq) (1.93 mL) and dioxane (3.44 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 (40.5 mg, 30%). 1H-NMR (400 MHz, d6-DMSO) δ (ppm) 2.96 (4H, m), 3.79 (4H, m), 7.28 (2H, d), 7.45 (1H, m), 7.54 (1H, br s), 8.01-8.09 (1H, dd), 8.25 (1H, s), 8.50 (1H, d), 8.69 (1H, br s), 8.78 (1H, s), 9.98 (1H, s), 13.3 (1H, br s). LCMS: Rt 2.23 min (96.9%), m/z (APCI) 406 (M+H)+.

後処理

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

出典と根拠

ORDレコード
ord-5b177b5c589646038abde62b94596b4e
出典データセット
uspto-grants-2011_03
特許番号
US07915256B2

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