4-Methylmorpholine → HCID 68157988, compound

HRID 242954Notes

Reaction equation

HRID 242954 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:5]([NH2:8])=[CH:6][CH:7]=1.[C:16]([O:20][C:21](CN[C@@H](C)C(O)=O)=[O:22])([CH3:19])([CH3:18])[CH3:17].[CH:30]1C=NC2N(O)N=NC=2C=1.[CH3:40][N:41]1CC[O:44][CH2:43][CH2:42]1.Cl.CN(C)CCCN=C=NCC>C(Cl)Cl>[C:16]([O:20][C:21](=[O:22])[N:41]([C@H:42]([C:43](=[O:44])[NH:8][C:5]1[CH:6]=[CH:7][C:2]([F:1])=[CH:3][C:4]=1[NH:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[CH3:30])[CH3:40])([CH3:17])([CH3:18])[CH3:19]

Participants

7

Reactant 5

HCID 79724-MethylmorpholineHCID 181649HOAtHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 214506204-Fluoro-2-phenylaminoanilineHCID 23563147HCID 23563147, compound

Product 1

HCID 68157988HCID 68157988, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 4-fluoro-N2-phenylbenzene-1,2-diamine (450 mg, 2.2 mmol), (S)-2-(tertbutoxycarbonylmethylamino)propionic acid (0.50 g, 2.4 mmol), HOAt (0.33 g, 2.4 mmol), 4-methylmorpholine (0.5 mL, 4.8 mmol) and N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (0.46 g, 2.4 mmol) in DCM (10 mL) was stirred at RT for 2 h. The reaction mixture was partitioned between DCM and a saturated aqueous solution of NaHCO3. The organic layer was washed with brine, dried (MgSO4), concentrated in vacuo and the resulting residue purified by column chromatography (Si—PCC, gradient 0-30% EtOAc in cyclohexane) to afford [(S)-1-(4-fluoro-2-phenylaminophenylcarbamoyl)ethyl]methylcarbamic acid tert-butyl ester (0.781 g, 92%). LCMS (Method J): RT 3.92 min [M+H]+ 388.1.

Workup

  1. customThe reaction mixture was partitioned between DCM
  2. washThe organic layer was washed with brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customthe resulting residue purified by column chromatography (Si—PCC, gradient 0-30% EtOAc in cyclohexane)

Sources & evidence

ORD record
ord-39eb30f1f16a4172ab9553323d16ea67
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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