Sodium Carbonate → 5-(5-Methyl-1H-pyrazol-4-yl)-N-(4-morpholinophenyl)-[1,2,4]triazolo[1,5-a]pyrazin-8-amine

HRID 605903

反応式

HRID 605903 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)=[CH:19]N=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:48]=[CH:47][C:46]([N:49]3[CH2:54][CH2:53][O:52][CH2:51][CH2:50]3)=[CH:45][CH:44]=2)=[N:35][CH:34]=1.CC1NN=CC=1B1OC(C)(C)C(C)(C)O1.C([O-])([O-])=O.[Na+].[Na+]>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].[CH3:19][C:18]1[NH:17][N:29]=[CH:30][C:21]=1[C:33]1[N:38]2[N:39]=[CH:40][N:41]=[C:37]2[C:36]([NH:42][C:43]2[CH:48]=[CH:47][C:46]([N:49]3[CH2:54][CH2:53][O:52][CH2:51][CH2:50]3)=[CH:45][CH:44]=2)=[N:35][CH:34]=1

参加物

8

反応物 4

HCID 10340Sodium CarbonateHCID 177502703-Methyl-1H-pyrazole-4-boronic acid pinacol esterHCID 575899284-{8-[4-(4-Methyl-piperazin-1-yl)-phenylamino]-[1,2,4]triazolo[1,5-a]pyrazin-5-yl}-thiophene-2-carboxylic acid amideHCID 57589931(5-Bromo-[1,2,4]triazolo[1,5-a]pyrazin-8-yl)-(4-morpholin-4-ylphenyl)amine

生成物 2

HCID 222AmmoniaHCID 1359004475-(5-Methyl-1H-pyrazol-4-yl)-N-(4-morpholinophenyl)-[1,2,4]triazolo[1,5-a]pyrazin-8-amine収率 7.5%

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒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-bromo-[1,2,4]triazolo[1,5-a]pyrazin-8-yl)-(4-morpholin-4-yl-phenyl)-amine (0.2 g, 0.53 mmol), 5-methyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrazole (222 mg, 1.06 mmol), and Pd(PPh3)4 (0.154 mg, 0.134 mmol) in 1.5M Na2CO3 (aq) (2.84 mL, 4.26 mmol) and dioxane (8.5 mL). The reaction mixture is purified by silica gel column chromatography using 98:2 and 97:3 DCM:NH3 (7M in MeOH) to give the title compound (15 mg, 7.5%). Conversion into the mesylate salt using 0.1M methanesulfonic acid in MeOH (0.398 mL) affords the title compound (15 mg) as a pale green solid. 1H-NMR (400 MHz, d6-DMSO) δ (ppm) 2.41 (3H, s, MsOH), 2.46 (3H, s), 3.20 (4H, m), 3.71 (4H, m), 7.11 (2H, d), 7.74 (1H, s), 7.97 (2H, d), 8.15 (1H, s), 8.69 (1H, s), 9.88 (1H, s). LCMS: Rt 2.41 min (98.3%), m/z (APCI) 377 (M+H)+.

後処理

  1. customThis compound may be prepared
  2. customThe reaction mixture is purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-8fb1d274f056461ea7459b58081a5a11
出典データセット
uspto-grants-2011_03
特許番号
US07915256B2

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