4-Methylmorpholine → HCID 57959382, compound

HRID 2091451Notes

Reaction equation

HRID 2091451 reaction equation
[NH2:1][CH2:2][C:3]1[CH:4]=[C:5]([S:9]([NH:12][CH2:13][CH2:14][NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])(=[O:11])=[O:10])[CH:6]=[CH:7][CH:8]=1.[C:23]1([C:29]2[N:34]=[CH:33][C:32]([C:35](O)=[O:36])=[CH:31][N:30]=2)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C1C=CC2N(O)N=NC=2C=1.CN1CCOCC1.Cl.CN(CCCN=C=NCC)C>CN(C)C=O.C(OCC)(=O)C>[C:23]1([C:29]2[N:34]=[CH:33][C:32]([C:35]([NH:1][CH2:2][C:3]3[CH:4]=[C:5]([S:9]([NH:12][CH2:13][CH2:14][NH:15][C:16](=[O:22])[O:17][C:18]([CH3:19])([CH3:21])[CH3:20])(=[O:10])=[O:11])[CH:6]=[CH:7][CH:8]=3)=[O:36])=[CH:31][N:30]=2)[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

8

Reactant 5

HCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 7473892-Phenylpyrimidine-5-carboxylic acid2×HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 57959390HCID 57959390, compound2×

Product 1

HCID 57959382HCID 57959382, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture consisting of tert-butyl 2-(3-(aminomethyl)phenylsulfonamido)ethylcarbamate (Compound 16, 278 mg), 2-phenylpyrimidine-5-carboxylic acid (Compound 17; synthesis described in Example 1, Steps 1-3 of WO 2007/041634 to Aldous et al., entitled “Pyrimidine Amide Compounds as PGDS Inhibitors”; 182 mg), HOBt (123 mg), and N-methyl-morpholine (0.11 mL) in N,N-dimethylformamide (11 mL) was added 1-(dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (287 mg) and the mixture was stirred for 2.5 hours. The crude reaction mixture was diluted with ethyl acetate and washed with brine. The organic phase was dried (MgSO4), filtered and concentrated under reduced pressure. The residue was purified by silica chromatography (5:95 methanol-dichloromethane) to afford the title intermediate (363 mg, 87%); MS (ESI−) m/z 510 (M−1).

Workup

  1. customThe crude reaction mixture
  2. washwashed with brine
  3. dry with materialThe organic phase was dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica chromatography (5:95 methanol-dichloromethane)

Sources & evidence

ORD record
ord-a4c495fe319943ffbba49c425690a7b5
Source dataset
uspto-grants-2013_05
Patent number
US08440417B2

Reaction notes

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