1,2-Dichloroethane → HCID 59373964, compound

HRID 473716Notes

Reaction equation

HRID 473716 reaction equation
[CH3:1][O:2][CH2:3][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].[CH:33]1C=CC2N(O)N=NC=2C=1.CO[C@H](C)C(O)=O.C(N(C(C)C)CC)(C)C.C(Cl)CCl>C(Cl)Cl>[CH3:1][O:2][C@H:3]([CH3:33])[C:4]([N:6]1[CH2:7][CH2:8][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)[CH2:10][CH2:11]1)=[O:5]

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 2733584(2R)-2-methoxypropanoic acidHCID 593742462-Methoxy-1-(4-(3-(4-(5-methylpyridin-2-ylamino)phenoxy)pyrazin-2-YL)piperidin-1-YL)ethanone

Product 1

HCID 59373964HCID 59373964, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 5-methyl-N-(4-(3-(piperidin-4-yl)pyrazin-2-yloxy)phenyl)pyridin-2-amine (3.58 mL, 0.394 mmol) (See step 3, Example 282), HOBT (0.015 g, 0.099 mmol), (R)-2-methoxypropanoic acid (0.049 g, 0.473 mmol), diisopropylethylamine (0.364 mL, 2.090 mmol), and EDC (0.091 g, 0.473 mmol) in DCM (5 mL) was stirred at RT overnight. The reaction mixture was concentrated in vacuo, then taken up in H2O. The solid was collected by filtration, air-dried and purified by ISCO column (75% EtOAc/Hexanes) to give the title compound. MS (ESI, pos. ion) m/z: 448.2 (M+1). IC50 (uM) 0.000452.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. filtrationThe solid was collected by filtration
  3. customair-dried
  4. custompurified by ISCO column (75% EtOAc/Hexanes)

Sources & evidence

ORD record
ord-2b62b6bd998e4e4bbaf9099193fded25
Source dataset
uspto-grants-2014_01
Patent number
US08637500B2

Reaction notes

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