Sodium t-butoxide → 5-(5-Bromo-imidazo[1,2-a]pyrazin-8-ylamino)-pyridine-2-carboxylic acid (2-diethylamino-ethyl)-amide

HRID 1366126

反応式

HRID 1366126 の反応式
OC1C=CC(C[NH:7]C(=O)C2C=CC(NC3C4N(C=CN=4)C(C4C=NNC=4)=CN=3)=CC=2)=CC=1.[Br:33][C:34]1[N:39]2[CH:40]=[CH:41][N:42]=[C:38]2[C:37](Br)=[N:36][CH:35]=1.[CH2:44]([N:46]([CH2:59][CH3:60])[CH2:47][CH2:48][NH:49][C:50]([C:52]1[CH:57]=[CH:56][C:55]([NH2:58])=[CH:54][N:53]=1)=[O:51])[CH3:45].CC([O-])(C)C.[Na+]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.C1(C)C=CC=CC=1>[NH3:7].[CH2:59]([N:46]([CH2:44][CH3:45])[CH2:47][CH2:48][NH:49][C:50]([C:52]1[CH:57]=[CH:56][C:55]([NH:58][C:37]2[C:38]3[N:39]([CH:40]=[CH:41][N:42]=3)[C:34]([Br:33])=[CH:35][N:36]=2)=[CH:54][N:53]=1)=[O:51])[CH3:60]

参加物

9

反応物 4

HCID 23676156Sodium t-butoxideHCID 24857547N-(4-Hydroxybenzyl)-4-[5-(1H-pyrazol-4-yl)imidazo[1,2-a]pyrazin-8-ylamino]benzamideHCID 534859495,8-Dibromoimidazo[1,2-a]pyrazineHCID 590231165-Amino-pyridine-2-carboxylic acid (2-diethylamino-ethyl)-amide

生成物 2

HCID 222AmmoniaHCID 590231155-(5-Bromo-imidazo[1,2-a]pyrazin-8-ylamino)-pyridine-2-carboxylic acid (2-diethylamino-ethyl)-amide収率 72%

試薬・触媒・溶媒 3

HCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)触媒HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 1140Toluene溶媒

実験手順

In the same way as described for Compound 90, step 1, using 5,8-dibromoimidazo[1,2-a]pyrazine (0.272 g, 0.982 mmol), 5-amino-pyridine-2-carboxylic acid (2-diethylamino-ethyl)-amide (0.197 g, 0.835 mmol), NaOtBu (0.132 g, 1.37 mmol), Pd2(dba)3 (18 mg, 0.02 mmol), Xantphos (22 mg, 0.038 mmol) and toluene (3 mL). The crude material is purified by silica gel column chromatography eluting with DCM followed by 94:6 DCM:NH3 (7M in MeOH) to afford the title compound (0.263 g, 72%). HPLC (254 nm) Rt 2.09 min (72%).

後処理

  1. customThe crude material is purified by silica gel column chromatography
  2. washeluting with DCM

出典と根拠

ORDレコード
ord-645031713f7447d1b96085545a24359c
出典データセット
uspto-grants-2011_02
特許番号
US07893058B2

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