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 535410Notes

Reaction equation

HRID 535410 reaction equation
[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]

Participants

7

Reactant 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

Product 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

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

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).

Workup

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

Sources & evidence

ORD record
ord-caccdb74d2ce4f15978253b51e723249
Source dataset
uspto-grants-2014_10
Patent number
US08859541B2

Reaction notes

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