Diisopropylethylamine → tert-butyl-N-methyl-N-[1-[[5-(2-methylimidazo[1,2-a]pyridin-3-yl)-6-[2-(1-methyl-2-oxoquinolin-6-yl)ethynyl]pyridin-2-yl]amino]-1-oxopropan-2-yl]-carbamate

HRID 535410노트

반응식

HRID 535410 반응식
[C:1]([O:5][C:6](=[O:32])[N:7]([CH:9]([CH3:31])[C:10]([NH:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[N:23]3[CH:24]=[CH:25][CH:26]=[CH:27][C:22]3=[N:21][C:20]=2[CH3:28])=[C:15]([C:29]#[CH:30])[N:14]=1)=[O:11])[CH3:8])([CH3:4])([CH3:3])[CH3:2].Br[C:34]1[CH:35]=[C:36]2[C:41](=[CH:42][CH:43]=1)[N:40]([CH3:44])[C:39](=[O:45])[CH:38]=[CH:37]2.CCN(C(C)C)C(C)C>CN1C(=O)CCC1.[Cu]I.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[C:1]([O:5][C:6](=[O:32])[N:7]([CH3:8])[CH:9]([CH3:31])[C:10]([NH:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[N:23]3[CH:24]=[CH:25][CH:26]=[CH:27][C:22]3=[N:21][C:20]=2[CH3:28])=[C:15]([C:29]#[C:30][C:34]2[CH:35]=[C:36]3[C:41](=[CH:42][CH:43]=2)[N:40]([CH3:44])[C:39](=[O:45])[CH:38]=[CH:37]3)[N:14]=1)=[O:11])([CH3:4])([CH3:3])[CH3:2]

참가 물질

7

반응물 3

HCID 81531DiisopropylethylamineHCID 218161626-Bromo-1-methylquinolin-2(1H)-oneHCID 86694391tert-butyl-N-[1-[[6-ethynyl-5-(2-methylimidazo[1,2-a]pyridin-3-yl)pyridin-2-yl]amino]-1-oxopropan-2-yl]-N-methylcarbamate

생성물 1

HCID 86694397tert-butyl-N-methyl-N-[1-[[5-(2-methylimidazo[1,2-a]pyridin-3-yl)-6-[2-(1-methyl-2-oxoquinolin-6-yl)ethynyl]pyridin-2-yl]amino]-1-oxopropan-2-yl]-carbamate

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 178418476HCID 178418476, 화합물촉매HCID 13387N-methyl-2-pyrrolidone용매

실험 절차

A mixture of tert-butyl-N-[1-[[6-ethynyl-5-(2-methylimidazo[1,2-a]pyridin-3-yl)pyridin-2-yl]amino]-1-oxopropan-2-yl]-N-methylcarbamate F1a (60 mg, 0.14 mmol), 6-bromo-1-methylquinolin-2-one (82 mg, 0.35 mmol), copper(I) iodide (2.6 mg, 0.01 mmol), Dichlorobis(triphenylphosphine)palladium(II) (8.1 mg, 0.01 mmol) and DIPEA (94 μl, 0.55 mmol) is stirred under argon atmosphere in NMP (0.5 ml) for 2 h at 50° C. The mixture is concentrated in vacuo and the product purified by RP HPLC. Yield: 17 mg (21%). HPLC-MS: M+H=591; tR=1.79 min (*Method—4).

후처리

  1. concentrationThe mixture is concentrated in vacuo
  2. customthe product purified by RP HPLC

출처 및 근거

ORD 기록
ord-caccdb74d2ce4f15978253b51e723249
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08859541B2

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