4-Methylmorpholine → HCID 66775523, compound

HRID 1645256Notes

Reaction equation

HRID 1645256 reaction equation
Cl[C:2]1[C:3]2[N:4]([C:8]([CH2:12][CH2:13][C:14]([OH:16])=O)=[N:9][C:10]=2[I:11])[CH:5]=[CH:6][N:7]=1.[CH2:17]([NH:19][CH2:20][CH2:21][OH:22])[CH3:18].Cl.C(N=C=NCCCN(C)C)C.O.[OH:36][N:37]1[C:41]2[CH:42]=[CH:43][CH:44]=[CH:45][C:40]=2[N:39]=[N:38]1.CN1CCOCC1>CN(C=O)C>[N:37]1([O:36][C:2]2[C:3]3[N:4]([C:8]([CH2:12][CH2:13][C:14]([N:19]([CH2:17][CH3:18])[CH2:20][CH2:21][OH:22])=[O:16])=[N:9][C:10]=3[I:11])[CH:5]=[CH:6][N:7]=2)[C:41]2[CH:42]=[CH:43][CH:44]=[CH:45][C:40]=2[N:39]=[N:38]1

Participants

7

Reactant 5

HCID 79724-MethylmorpholineHCID 80722-(Ethylamino)ethanolHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 76849808HCID 76849808, compound

Product 1

HCID 66775523HCID 66775523, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of EXAMPLE 74B (1.3 g), 2-(ethylamino)ethanol (0.363 g), 1-ethyl-3-(3-(dimethylamino)propyl)-carbodiimide hydrochloride (0.78 g), 1-hydroxybenzotriazole hydrate (0.623 g), and N-methylmorpholine (0.748 g) in 5 mL DMF was stirred at room temperature for 10 hours. The reaction mixture was extracted with ethyl acetate 3 times and the combined extracts were washed (brine), dried (MgSO4) and concentrated. The residue was purified by flash chromatography with 0-4% methanol/CH2Cl2 to afford 3-(8-(1H-benzo(d)(1,2,3)triazol-1-yloxy)-1-iodoimidazo[1,5-a]pyrazin-3-yl)-N-ethyl-N-(2-hydroxyethyl)propanamide. MS (ESI(+)) m/e 522 (M+H)+ This product was placed in a high pressure tube with 7N ammonia (15 ml) in methanol, heated at 60 C overnight then concentrated to dryness. The residue was purified by flash column with 0-10% methanol/CH2Cl2 to give the title compound. MS (ESI(+)) m/e 404 (M+H)+

Workup

  1. extractionThe reaction mixture was extracted with ethyl acetate 3 times
  2. washthe combined extracts were washed (brine)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. customThe residue was purified by flash chromatography with 0-4% methanol/CH2Cl2

Sources & evidence

ORD record
ord-a7e88379b2e343479100d5ccb3db7d1a
Source dataset
uspto-grants-2012_02
Patent number
US08124759B2

Reaction notes

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