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

HRID 1366126

반응식

HRID 1366126 반응식
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]

참가 물질

9

반응물 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

생성물 2

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

시약·촉매·용매 3

HCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)촉매HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 1140Toluene용매

실험 절차

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%).

후처리

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

출처 및 근거

ORD 기록
ord-645031713f7447d1b96085545a24359c
출처 데이터셋
uspto-grants-2011_02
특허 번호
US07893058B2

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