4-Methylmorpholine → HCID 178508752, compound

HRID 1665130Notes

Reaction equation

HRID 1665130 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-0fb707954982463e8f13b893f52a4bbb
Source dataset
uspto-grants-2011_10
Patent number
US08039472B2

Reaction notes

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