4-Methylmorpholine → ((S)-1-{[(3,5-Diamino-6-chloro-pyrazine-2-carbonyl)-amino]-methyl}-butyl)-carbamic acid tert-butyl ester

HRID 882904Notes

Reaction equation

HRID 882904 reaction equation
[C:1]([O:5][C:6](=[O:14])[NH:7][C@H:8]([CH2:12][NH2:13])[CH2:9][CH2:10][CH3:11])([CH3:4])([CH3:3])[CH3:2].[NH2:15][C:16]1[C:17]([C:24](O)=[O:25])=[N:18][C:19]([Cl:23])=[C:20]([NH2:22])[N:21]=1.CN1CCOCC1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[C:1]([O:5][C:6](=[O:14])[NH:7][C@H:8]([CH2:12][NH:13][C:24]([C:17]1[C:16]([NH2:15])=[N:21][C:20]([NH2:22])=[C:19]([Cl:23])[N:18]=1)=[O:25])[CH2:9][CH2:10][CH3:11])([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 4

HCID 79724-MethylmorpholineHCID 64521193,5-Diamino-6-chloro-pyrazine acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 86651886((S)-1-Aminomethyl-butyl)-carbamic acid tert-butyl ester

Product 1

HCID 86651887((S)-1-{[(3,5-Diamino-6-chloro-pyrazine-2-carbonyl)-amino]-methyl}-butyl)-carbamic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of ((S)-1-aminomethyl-butyl)-carbamic acid tert-butyl ester (1.70 g, 8.40 mmol), 3,5-diamino-6-chloro-pyrazine-2-carboxylic acid (1.59 g, 8.43 mmol), N-methylmorpholine (3.8 mL, 34.5 mmol) and HATU (3.2 g, 8.42 mmol) in anhydrous DMF (50 mL) is stirred at RT for 16 h. The reaction mixture is concentrated in vacuo and the resulting residue is purified by column chromatography (basic alumina, MeOH:DCM) to afford the title compound as yellow solid. [M+H]+ 333.

Workup

  1. concentrationThe reaction mixture is concentrated in vacuo
  2. customthe resulting residue is purified by column chromatography (basic alumina, MeOH:DCM)

Sources & evidence

ORD record
ord-0785a7067f62486383ec4c2d1e69cfe6
Source dataset
uspto-grants-2012_08
Patent number
US08236808B2

Reaction notes

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