Sodium Carbonate → 5-{8-[4-(4-Methyl-piperazin-1-yl)-phenylamino]-[1,2,4]triazolo[1,5-a]pyrazin-5-yl}-thiophene-2-carboxylic acid amide

HRID 605902

反応式

HRID 605902 の反応式
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:13]=[CH:12][C:11]([NH:14][C:15]3[C:16]4[N:17]([N:29]=[CH:30][N:31]=4)[C:18](C4C=C(C(N)=O)SC=4)=[CH:19][N:20]=3)=[CH:10][CH:9]=2)[CH2:4][CH2:3]1.CN1CCN(C2C=CC(N)=CC=2)CC1.CC1(C)C(C)(C)OB([C:54]2[S:58][C:57]([C:59]([NH2:61])=[O:60])=[CH:56][CH:55]=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>[NH3:2].[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:9]=[CH:10][C:11]([NH:14][C:15]3[C:16]4[N:17]([N:29]=[CH:30][N:31]=4)[C:18]([C:54]4[S:58][C:57]([C:59]([NH2:61])=[O:60])=[CH:56][CH:55]=4)=[CH:19][N:20]=3)=[CH:12][CH:13]=2)[CH2:4][CH2:3]1

参加物

8

反応物 4

HCID 10340Sodium CarbonateHCID 7372534-(4-Methylpiperazin-1-yl)anilineHCID 575899284-{8-[4-(4-Methyl-piperazin-1-yl)-phenylamino]-[1,2,4]triazolo[1,5-a]pyrazin-5-yl}-thiophene-2-carboxylic acid amideHCID 575899405-(Tetramethyl-1,3,2-dioxaborolan-2-yl)thiophene-2-carboxamide

生成物 2

HCID 222AmmoniaHCID 575900115-{8-[4-(4-Methyl-piperazin-1-yl)-phenylamino]-[1,2,4]triazolo[1,5-a]pyrazin-5-yl}-thiophene-2-carboxylic acid amide収率 21%

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-(4-methyl-piperazin-1-yl)-phenyl]-amine (100 mg, 0.258 mmol), 5-(4,4,5,5-tetramethyl-[1,3,2]dioxa-borolan-2-yl)-thiophene-2-carboxylic acid amide (130 mg, 0.516 mmol) and Pd(PPh3)4 (74 mg, 0.0645 mmol) in aqueous 1.5M Na2CO3 (1.37 mL, 2.06 mmol) and dioxane (2.75 mL). After evaporation of the solvent, the residue is purified by silica gel column chromatography eluting with 96:6 DCM:NH3 (7M in MeOH) to afford the title compound (23 mg, 21%). LCMS: Rt 1.94 min (97.9%). 1H-NMR (400 MHz, d6-DMSO) δ (ppm) 2.26 (3H, s), 2.49 (4H, m), 3.14 (4H, m), 6.98 (2H, d), 7.51 (1H, br s), 7.85-7.89 (2H, m), 8.03 (2H, d), 8.10 (1H, br s), 8.38 (1H, s), 8.82 (1H, s), 10.10 (1H, s). LCMS: Rt 1.94 min, (97.9%), m/z (APCI) 435 (M+H)+.

後処理

  1. customThis compound may be prepared
  2. customAfter evaporation of the solvent
  3. customthe residue is purified by silica gel column chromatography
  4. washeluting with 96:6 DCM

出典と根拠

ORDレコード
ord-6e553980a417495c9a52989bf26bcfb4
出典データセット
uspto-grants-2011_03
特許番号
US07915256B2

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