4-Methylmorpholine → HCID 86656656, compound

HRID 882913Notes

Reaction equation

HRID 882913 reaction equation
[NH2:1][C:2]1[C:3]([C:10]([OH:12])=O)=[N:4][C:5]([Cl:9])=[C:6]([NH2:8])[N:7]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CN1CCOCC1.C(OC(=O)[NH:50][C@H:51]([CH2:59][NH2:60])[CH2:52][C:53]1[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=1)(C)(C)C>CN(C=O)C>[NH2:50][C@@H:51]([CH2:52][C:53]1[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=1)[CH2:59][NH:60][C:10]([C:3]1[C:2]([NH2:1])=[N:7][C:6]([NH2:8])=[C:5]([Cl:9])[N:4]=1)=[O:12]

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 10422234(S)-tert-Butyl (1-amino-3-phenylpropan-2-yl)carbamate

Product 1

HCID 86656656HCID 86656656, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3,5-diamino-6-chloro-pyrazine-2-carboxylic acid (0.225 g, 1.2 mmol) and HATU (0.46 g, 1.2 mmol) in DMF (10 mL) is added N-methylmorpholine (0.53 mL, 4.8 mmol) and ((S)-1-aminomethyl-2-phenyl-ethyl)-carbamic acid tert-butyl ester (0.3 g, 1.2 mmol) and the resulting yellow solution is stirred at RT for 18 h. The solvent is removed in vacuo and the residue is diluted with water (10 mL). The precipitate which forms is collected by filtration and dissolved in DCM (5 mL). TFA (1 mL) is added and the solution stirred at RT for 1 h. The solvent is removed in vacuo, and the residue is purified by reverse phase chromatography (Isolute™ C18, 0-100% acetonitrile in water with 0.1% TFA) to yield the title compound. [M+H]+ 321

Workup

  1. customThe solvent is removed in vacuo
  2. additionthe residue is diluted with water (10 mL)
  3. filtrationThe precipitate which forms is collected by filtration
  4. dissolutiondissolved in DCM (5 mL)
  5. additionTFA (1 mL) is added
  6. stirringthe solution stirred at RT for 1 h
  7. customThe solvent is removed in vacuo
  8. customthe residue is purified by reverse phase chromatography (Isolute™ C18, 0-100% acetonitrile in water with 0.1% TFA)

Sources & evidence

ORD record
ord-8365cdb8f39e4fb2bda35053084c7b70
Source dataset
uspto-grants-2012_08
Patent number
US08236808B2

Reaction notes

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