4-Methylmorpholine → HCID 178508752, compound

HRID 2365517Notes

Reaction equation

HRID 2365517 reaction equation
[NH2:1][C:2]1[C:3]([C:10](/[N:12]=[C:13]2\[NH:14][CH2:15][C:16]3([CH2:23][CH:22]4[NH:24][CH:19]([CH2:20][CH2:21]4)[CH2:18]3)[NH:17]\2)=[O:11])=[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.[NH:49]1[C:57]2[CH:56]=[CH:55][CH:54]=[C:53]([C:58](O)=[O:59])[C:52]=2[CH:51]=[CH:50]1.CN1CCOCC1>CN(C=O)C>[NH:49]1[C:57]2[CH:56]=[CH:55][CH:54]=[C:53]([C:58]([N:24]3[CH:22]4[CH2:21][CH2:20][CH:19]3[CH2:18][C:16]3([CH2:23]4)[CH2:15][NH:14]/[C:13](=[N:12]\[C:10]([C:3]4[C:2]([NH2:1])=[N:7][C:6]([NH2:8])=[C:5]([Cl:9])[N:4]=4)=[O:11])/[NH:17]3)=[O:59])[C:52]=2[CH:51]=[CH:50]1

Participants

6

Reactant 4

HCID 79724-MethylmorpholineHCID 595229Indole-4-carboxylic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 178508756HCID 178508756, compound

Product 1

HCID 178508752HCID 178508752, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(E)-3,5-diamino-6-chloro-N-(8-azaspiro[bicyclo[3.2.1]octane-3,4′-imidazolidine]-2′-ylidene)pyrazine-2-carboxamide (170 mg, 0.49 mmol) is dissolved in DMF (10 ml) along with HATU (184 mg, 0.49 mmol) and 4-indole-carboxylic acid (78 mg, 0.49 mmol). N-Methyl morpholine (160 ml, 1.45 mmol) is added and the solution stirred at room temperature overnight. The mixture is then concentrated in vacuo. EtOAc (100 ml) is added and the solution washed with water (100 ml). The organic phase is dried (MgSO4) and concentrated in vacuo. Purification by flash chromatography (SiO2, DCM/MeOH) gives the title compound as a yellow solid; [M+H]+ 494.15, 496.27 for Cl isotopes.

Workup

  1. concentrationThe mixture is then concentrated in vacuo
  2. additionEtOAc (100 ml) is added
  3. washthe solution washed with water (100 ml)
  4. dry with materialThe organic phase is dried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customPurification by flash chromatography (SiO2, DCM/MeOH)

Sources & evidence

ORD record
ord-84c31e89ca6d4f9185382ac362ac830d
Source dataset
uspto-grants-2014_04
Patent number
US08697687B2

Reaction notes

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