4-Methylmorpholine → HCID 68157210, compound

HRID 242866Notes

Reaction equation

HRID 242866 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([NH2:15])[C:5]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:6][CH:7]=1.[C:16]([O:20][C:21]([NH:23][C@@H:24]([CH3:28])[C:25](O)=[O:26])=[O:22])([CH3:19])([CH3:18])[CH3:17].C1C=NC2N(O)N=NC=2C=1.CN1CCOCC1.Cl.CN(C)CCCN=C=NCC>C(Cl)Cl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[C:4]([NH:15][C:25](=[O:26])[C@@H:24]([NH:23][C:21](=[O:22])[O:20][C:16]([CH3:18])([CH3:17])[CH3:19])[CH3:28])[CH:3]=1

Participants

7

Reactant 5

HCID 79724-MethylmorpholineHCID 85082Tert-butoxycarbonylalanineHCID 181649HOAtHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 19043380HCID 19043380, compound

Product 1

HCID 68157210HCID 68157210, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 4-fluoro-N1-phenylbenzene-1,2-diamine (866 mg, 4.3 mmol), (S)-2-tertbutoxycarbonylaminopropionic acid (890 mg, 4.7 mmol), HOAt (640 mg, 4.7 mmol), 4-methylmorpholine (1.0 mL, 9.5 mmol) and N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (900 mg, 4.7 mmol) in DCM (20 mL) was stirred at RT for 2 h. The reaction mixture was then partitioned between DCM (50 mL) and a saturated solution of NaHCO3. The organic layer was washed with brine, then dried (MgSO4) and concentrated in vacuo affording (S)-tert-butyl 1-(5-fluoro-2-(phenylamino)phenylamino)-1-oxopropan-2-ylcarbamate as a yellow-orange solid (quantitative), used in the following step without further purification. LCMS: RT 3.83 min [M+H]+ 374.1

Workup

  1. customThe reaction mixture was then partitioned between DCM (50 mL)
  2. washThe organic layer was washed with brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-462fdcfa1d5f4ee5b4d6579038284db3
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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