Pyridine → HCID 58547081, compound

HRID 1850323Notes

Reaction equation

HRID 1850323 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[N:11]1[CH2:14][CH:13]([C:15]2[C:16]([N:21]3[CH2:25][CH2:24][CH:23]([NH2:26])[CH2:22]3)=[N:17][CH:18]=[CH:19][N:20]=2)[CH2:12]1.N1C=CC=CC=1.N1(C2C=CN=CC=2)CCCC1.[C:44](Cl)(=[O:47])[O:45][CH3:46]>C(Cl)Cl>[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[N:11]1[CH2:12][CH:13]([C:15]2[C:16]([N:21]3[CH2:25][CH2:24][CH:23]([NH:26][C:44](=[O:47])[O:45][CH3:46])[CH2:22]3)=[N:17][CH:18]=[CH:19][N:20]=2)[CH2:14]1

Participants

6

Reactant 4

HCID 1049PyridineHCID 6586Methyl chloroformateHCID 755674-PyrrolidinopyridineHCID 58546840HCID 58546840, compound

Product 1

HCID 58547081HCID 58547081, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a round bottomed flask was added 1-(3-(1-(quinolin-2-yl)azetidin-3-yl)pyrazin-2-yl)pyrrolidin-3-amine (0.0974 g, 0.281 mmol), pyridine (commercially available through Aldrich, 0.045 ml, 0.562 mmol), and 4-(pyrrolidin-1-yl)pyridine (PPY) (commercially available through Alfa Aesar, 0.042 g, 0.281 mmol) to stir at RT in DCM (0.937 ml). Methyl carbonochloridate (commercially available through Aldrich, 0.027 ml, 0.422 mmol) was added and allowed to stir overnight. 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 6% MeOH in CH2Cl2, to provide methyl (1-(3-(1-(quinolin-2-yl)azetidin-3-yl)pyrazin-2-yl)pyrrolidin-3-yl)carbamate.

Workup

  1. customchromatographed through a Biotage 50 g SNAP HP-silica column
  2. washeluting with a gradient of 1% to 6% MeOH in CH2Cl2

Sources & evidence

ORD record
ord-ed113b8380d74f7d88d140d65c2aa2c1
Source dataset
uspto-grants-2015_02
Patent number
US08957073B2

Reaction notes

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