4-Methylmorpholine → HCID 86762290, compound

HRID 1183017Notes

Reaction equation

HRID 1183017 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.[CH3:44][O:45][C:46]1[CH:74]=[C:73]([O:75][CH3:76])[CH:72]=[CH:71][C:47]=1[CH2:48][NH:49][CH:50]([CH2:53][CH2:54][CH2:55][C:56]1[CH:61]=[CH:60][C:59]([O:62][CH2:63][C@@H:64]2[CH2:68][O:67][C:66]([CH3:70])([CH3:69])[O:65]2)=[CH:58][CH:57]=1)[CH2:51][NH2:52]>CN(C=O)C>[CH3:44][O:45][C:46]1[CH:74]=[C:73]([O:75][CH3:76])[CH:72]=[CH:71][C:47]=1[CH2:48][NH:49][CH:50]([CH2:53][CH2:54][CH2:55][C:56]1[CH:57]=[CH:58][C:59]([O:62][CH2:63][C@H:64]2[CH2:68][O:67][C:66]([CH3:70])([CH3:69])[O:65]2)=[CH:60][CH:61]=1)[CH2:51][NH:52][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 70654078HCID 70654078, compound

Product 1

HCID 86762290HCID 86762290, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3,5-diamino-6-chloro-pyrazine-2-carboxylic acid (161 mg, 0.86 mmol) and HATU (325 mg, 0.86 mmol) in DMF (10 mL) is added N-methylmorpholine (0.38 mL, 3.42 mmol) followed by N*2*-(2,4-dimethoxy-benzyl)-5-[4-((R)-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy)-phenyl]-pentane-1,2-diamine (391 mg, 0.86 mmol) and the mixture is stirred at RT overnight. The solvent is removed in vacuo. To the crude residue is added water (10 mL), which is then decanted off to leave an orange solid that is washed with diethyl ether (10 mL) and dried in vacuo at 50° C. to afford the title compound. [M+H]+ 629.

Workup

  1. customThe solvent is removed in vacuo
  2. additionTo the crude residue is added water (10 mL), which
  3. customis then decanted off
  4. customto leave an orange solid
  5. washthat is washed with diethyl ether (10 mL)
  6. customdried in vacuo at 50° C.

Sources & evidence

ORD record
ord-f39531e710904348a24f868962145c96
Source dataset
uspto-grants-2014_03
Patent number
US08664228B2

Reaction notes

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