Pyridine → HCID 58546757, compound

HRID 1850327Notes

Reaction equation

HRID 1850327 reaction equation
[CH3:1][NH:2][CH:3]1[CH2:7][CH2:6][N:5]([C:8]2[C:13]([CH:14]3[CH2:17][N:16]([C:18]4[CH:27]=[CH:26][C:25]5[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=5)[N:19]=4)[CH2:15]3)=[N:12][CH:11]=[CH:10][N:9]=2)[CH2:4]1.N1C=CC=CC=1.N1(C2C=CN=CC=2)CCCC1.[C:45](Cl)(=[O:48])[O:46][CH3:47]>C(Cl)Cl>[CH3:1][N:2]([CH:3]1[CH2:7][CH2:6][N:5]([C:8]2[C:13]([CH:14]3[CH2:17][N:16]([C:18]4[CH:27]=[CH:26][C:25]5[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=5)[N:19]=4)[CH2:15]3)=[N:12][CH:11]=[CH:10][N:9]=2)[CH2:4]1)[C:45](=[O:48])[O:46][CH3:47]

Participants

6

Reactant 4

HCID 1049PyridineHCID 6586Methyl chloroformateHCID 755674-PyrrolidinopyridineHCID 58546712HCID 58546712, compound

Product 1

HCID 58546757HCID 58546757, compoundYield 26.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

14 Mar. 2011 To a round bottomed flask was added N-methyl-1-(3-(1-(quinolin-2-yl)azetidin-3-yl)pyrazin-2-yl)pyrrolidin-3-amine (0.0999 g, 0.277 mmol), pyridine (0.045 ml, 0.554 mmol), and 4-(pyrrolidin-1-yl)pyridine (0.041 g, 0.277 mmol) to stir at RT in DCM (0.924 ml). Methyl carbonochloridate (0.027 ml, 0.416 mmol) was added and allowed to stir for 2 h. Solvent was evaporated and the crude product was adsorbed onto a plug of silica gel and chromatographed through a Biotage 50 g SNAP HP-silica column, eluting with a gradient of 1% to 4% MeOH in CH2Cl2, to provide methyl methyl(1-(3-(1-(quinolin-2-yl)azetidin-3-yl)pyrazin-2-yl)pyrrolidin-3-yl)carbamate (0.0307 g, 0.073 mmol, 26.5% yield).

Workup

  1. customSolvent was evaporated
  2. customchromatographed through a Biotage 50 g SNAP HP-silica column
  3. washeluting with a gradient of 1% to 4% MeOH in CH2Cl2

Sources & evidence

ORD record
ord-eb3bde49194449f6b8563df8897e9e82
Source dataset
uspto-grants-2015_02
Patent number
US08957073B2

Reaction notes

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