4-Methylmorpholine → HCID 86651898, compound

HRID 882914Notes

Reaction equation

HRID 882914 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:44]([O:48][C:49](=[O:69])[NH:50][C@H:51]([CH2:67][NH2:68])[CH2:52][CH2:53][CH2:54][CH2:55][NH:56][C:57]([O:59][CH2:60][C:61]1[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=1)=[O:58])([CH3:47])([CH3:46])[CH3:45]>CN(C=O)C.CO>[C:44]([O:48][C:49](=[O:69])[NH:50][C@H:51]([CH2:67][NH:68][C:10]([C:3]1[C:2]([NH2:1])=[N:7][C:6]([NH2:8])=[C:5]([Cl:9])[N:4]=1)=[O:12])[CH2:52][CH2:53][CH2:54][CH2:55][NH:56][C:57]([O:59][CH2:60][C:61]1[CH:62]=[CH:63][CH:64]=[CH:65][CH:66]=1)=[O:58])([CH3:47])([CH3:45])[CH3:46]

Participants

7

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 66916874HCID 66916874, compound

Product 1

HCID 86651898HCID 86651898, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 3,5-diamino-6-chloro-pyrazine-2-carboxylic acid (0.39 g, 2.05 mmol) and HATU (0.78 g, 2.05 mmol) in DMF (10 mL) is added N-methylmorpholine (0.83 g, 8.22 mmol) followed by ((S)-1-aminomethyl-5-benzyloxycarbonylamino-pentyl)-carbamic acid tert-butyl ester (prepared according to the procedure described in WO1997/01204 page 20) (750 mg, 2.05 mmol). The resulting solution is stirred at RT for 18 h and then concentrated in vacuo to afford an orange oil. The oil is dissolved in MeOH (10 mL) and allowed to stand at RT after which time a cream precipitate forms that is collected by filtration and dried under vacuum to yield the title compound. [M+H]+ 536.

Workup

  1. customprepared
  2. concentrationconcentrated in vacuo
  3. customto afford an orange oil
  4. customto stand at RT
  5. filtrationis collected by filtration
  6. customdried under vacuum

Sources & evidence

ORD record
ord-c9cb9d4ff6f54ebdbff22ae5492755f5
Source dataset
uspto-grants-2012_08
Patent number
US08236808B2

Reaction notes

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