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

HRID 605903

반응식

HRID 605903 반응식
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

참가 물질

8

반응물 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

생성물 2

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

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 312751,4-Dioxane용매

실험 절차

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)+.

후처리

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

출처 및 근거

ORD 기록
ord-8fb1d274f056461ea7459b58081a5a11
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07915256B2

연결된 노트

불러오는 중…