Methyl chloroformate → Methyl 4-(3-(4-(5-methylpyridin-2-ylamino)phenoxy)pyrazin-2-YL)piperidine-1-carboxylate

HRID 473715Notes

Reaction equation

HRID 473715 reaction equation
COC[C:4]([N:6]1[CH2:11][CH2:10][CH:9]([C:12]2[C:17]([O:18][C:19]3[CH:24]=[CH:23][C:22]([NH:25][C:26]4[CH:31]=[CH:30][C:29]([CH3:32])=[CH:28][N:27]=4)=[CH:21][CH:20]=3)=[N:16][CH:15]=[CH:14][N:13]=2)[CH2:8][CH2:7]1)=[O:5].C(N(C(C)C)CC)(C)C.Cl[C:43](OC)=[O:44]>C(Cl)Cl>[CH3:32][C:29]1[CH:30]=[CH:31][C:26]([NH:25][C:22]2[CH:23]=[CH:24][C:19]([O:18][C:17]3[C:12]([CH:9]4[CH2:10][CH2:11][N:6]([C:4]([O:44][CH3:43])=[O:5])[CH2:7][CH2:8]4)=[N:13][CH:14]=[CH:15][N:16]=3)=[CH:20][CH:21]=2)=[N:27][CH:28]=1

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 81531DiisopropylethylamineHCID 593742462-Methoxy-1-(4-(3-(4-(5-methylpyridin-2-ylamino)phenoxy)pyrazin-2-YL)piperidin-1-YL)ethanone

Product 1

HCID 59373960Methyl 4-(3-(4-(5-methylpyridin-2-ylamino)phenoxy)pyrazin-2-YL)piperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred mixture of 5-methyl-N-(4-(3-(piperidin-4-yl)pyrazin-2-yloxy)phenyl)pyridin-2-amine (0.278 g, 0.548 mmol) (See step 3, Example 282), and diisopropylethylamine (0.502 mL, 2.88 mmol) in DCM (5 mL) was added methyl chloroformate (0.051 mL, 0.658 mmol). The reaction mixture was stirred at RT for 2 h. The reaction mixture was purified by ISCO column (40% EtOAc/Hexanes) to give the title compound. MS (ESI, pos. ion) m/z: 420.2 (M+1). IC50 (uM) 0.000107.

Workup

  1. customThe reaction mixture was purified by ISCO column (40% EtOAc/Hexanes)

Sources & evidence

ORD record
ord-b85d826bbf214b1dacf87d6c9e951f9a
Source dataset
uspto-grants-2014_01
Patent number
US08637500B2

Reaction notes

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