Sodium Carbonate → Ammonia

HRID 1366208

反応式

HRID 1366208 の反応式
Br[C:2]1[N:7]2[CH:8]=[CH:9][N:10]=[C:6]2[C:5]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([N:18]3[CH2:23][CH2:22][O:21][CH2:20][CH2:19]3)=[CH:14][N:13]=2)=[N:4][CH:3]=1.CC1(C)C(C)(C)OB([C:32]2[CH:33]=[N:34][NH:35][CH:36]=2)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>[NH3:4].[O:21]1[CH2:22][CH2:23][N:18]([C:15]2[CH:16]=[CH:17][C:12]([NH:11][C:5]3[C:6]4[N:7]([CH:8]=[CH:9][N:10]=4)[C:2]([C:32]4[CH:33]=[N:34][NH:35][CH:36]=4)=[CH:3][N:4]=3)=[N:13][CH:14]=2)[CH2:19][CH2:20]1

参加物

7

反応物 3

HCID 10340Sodium CarbonateHCID 27740104-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 59023091(5-Bromo-imidazo[1,2-a]pyrazin-8-yl)-(5-morpholin-4-yl-pyridin-2-yl)-amine

生成物 2

HCID 222AmmoniaHCID 59023111N-(5-Morpholinopyridin-2-yl)-5-(1H-pyrazol-4-yl)imidazo[1,2-a]pyrazin-8-amine

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

In the same way as described for compound 127, step 4 using (5-bromo-imidazo[1,2-a]pyrazin-8-yl)-(5-morpholin-4-yl-pyridin-2-yl)-amine (100 mg, 0.266 mmol), 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrazole (77.6 mg, 0.4 mmol), Pd(PPh3)4 (77 mg, 0.066 mmol) and 1.5M Na2CO3 (1.42 mL, 2.13 mmol) in dioxane (4 mL). The crude compound is purified by silica gel column chromatography eluting with 96:4 DCM:NH3 (7M in MeOH) to afford the title compound which is triturated with diethyl ether (12.9 mg, 8%) and converted into the mesylate salt (6.1 mg, 38%) LCMS: Rt 1.95 min (96%), m/z (APCI) 363 (M+H)+, 1H-NMR (400 MHz, d6-DMSO) δ (ppm) 2.34 (3H, s, MsOH), 3.20 (4H, m), 3.83 (4H, m), 7.38 (1H, br s), 7.64 (1H, br s), 7.71 (1H, s), 7.86 (1H, d), 7.98 (1H, d), 8.04 (2H, m), 8.35 (2H, br s), 8.43 (1H, s).

後処理

  1. customThe crude compound is purified by silica gel column chromatography
  2. washeluting with 96:4 DCM

出典と根拠

ORDレコード
ord-d2e88059c92c46cd8c39393a1b5e398e
出典データセット
uspto-grants-2011_02
特許番号
US07893058B2

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