4-Aminocarbonylphenylboronic acid → 4-{8-[4-(4-Dimethylaminomethyl-[1,2,3]triazol-1-yl)-phenylamino]-imidazo[1,2-a]pyrazin-5-yl}-benzamide

HRID 1921789

反応式

HRID 1921789 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[CH:22]=[C:21]([CH2:23][N:24]([CH3:26])[CH3:25])[N:20]=[N:19]3)=[CH:14][CH:13]=2)=[N:4][CH:3]=1.[NH2:27][C:28]([C:30]1[CH:35]=[CH:34][C:33](B(O)O)=[CH:32][CH:31]=1)=[O:29]>CN(C=O)C.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>[CH3:25][N:24]([CH2:23][C:21]1[N:20]=[N:19][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:33]4[CH:34]=[CH:35][C:30]([C:28]([NH2:27])=[O:29])=[CH:31][CH:32]=4)=[CH:3][N:4]=3)=[CH:13][CH:14]=2)[CH:22]=1)[CH3:26]

参加物

5

反応物 2

HCID 27378114-Aminocarbonylphenylboronic acidHCID 59023092(5-Bromo-imidazo[1,2-a]pyrazin-8-yl)-[4-(4-dimethylaminomethyl-[1,2,3]triazol-1-yl)-phenyl]-amine

生成物 1

HCID 590230264-{8-[4-(4-Dimethylaminomethyl-[1,2,3]triazol-1-yl)-phenylamino]-imidazo[1,2-a]pyrazin-5-yl}-benzamide収率 7%

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 217120691,4-dioxane N,N-dimethylformamide溶媒

実験手順

In the same way as described for Compound 178, step 4, using (5-bromo-imidazo[1,2-a]pyrazin-8-yl)-[4-(4-dimethylaminomethyl-[1,2,3]triazol-1-yl)-phenyl]-amine (63 mg, 0.152 mmol), 4-(aminocarbonyl)phenylboronic acid (50.3 mg, 0.305 mmol) 1.5 M Na2CO3 (0.813 mL, 1.22 mmol) and Pd(PPh3)4 (44.0 mg, 0.0381 mmol) in (2:1) DMF-dioxane (1.8 mL). Purification of the crude material by Isolute FlashSilicaII Cartridge chromatography eluting with 95:5 DCM:NH3 (7M in MeOH) followed by reverse phase preparative HPLC, affords the title compound as a white solid (4.7 mg, 7%). LCMS: Rt 1.92 min (96%) m/z (APCI) 455 (M+H)+; 1H-NMR (400 MHz, d6-DMSO) δ (ppm) 2.24 (6H, s), 3.61 (2H, s), 7.51 (1H, br s), 7.64 (1H, s), 7.80 (1H, s), 7.85-7.91 (4H, m), 8.08-8.12 (3H, m), 8.16 (1H, br s), 8.36 (2H, d), 8.66 (1H, s), 10.09 (1H, s).

後処理

  1. customPurification of the crude material by Isolute FlashSilicaII Cartridge chromatography
  2. washeluting with 95:5 DCM

出典と根拠

ORDレコード
ord-3c12923dc4364104b98712e0bfbf149b
出典データセット
uspto-grants-2012_05
特許番号
US08173656B2

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