4-Methylmorpholine → (S)-1-(6-fluoro-7-methyl-1-phenyl-1H-benzoimidazol-2-yl)ethylamine dihydrochloride

HRID 242983Notes

Reaction equation

HRID 242983 reaction equation
[F:1][C:2]1[C:3]([CH3:16])=[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(OC([NH:24][C@@H:25]([CH3:29])[C:26](O)=O)=O)(C)(C)C.C1C=NC2N(O)N=NC=2C=1.CN1CCOCC1.[ClH:47].CN(C)CCCN=C=NCC>C(Cl)Cl.O>[ClH:47].[ClH:47].[F:1][C:2]1[CH:7]=[CH:6][C:5]2[N:8]=[C:26]([C@@H:25]([NH2:24])[CH3:29])[N:9]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)[C:4]=2[C:3]=1[CH3:16]

Participants

8

Reactant 5

HCID 79724-MethylmorpholineHCID 85082Tert-butoxycarbonylalanineHCID 181649HOAtHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 681575494-Fluoro-3-methyl-N2-phenylbenzene-1,2-diamine

Product 1

HCID 68157596(S)-1-(6-fluoro-7-methyl-1-phenyl-1H-benzoimidazol-2-yl)ethylamine dihydrochloride

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 4-fluoro-3-methyl-N2-phenylbenzene-1,2-diamine (600 mg, 2.77 mmol), (S)-2-tertbutoxycarbonylaminopropionic acid (577 mg, 3.05 mmol), HOAt (415 mg, 3.05 mmol), 4-methylmorpholine (0.67 mL, 6.1 mmol) and N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (586 mg, 3.05 mmol) in DCM (10 mL) was stirred at RT for 1 h. The reaction mixture was diluted with water and extracted with DCM (×3). The combined organic fractions were washed with brine, dried (MgSO4) and concentrated in vacuo.

Workup

  1. extractionextracted with DCM (×3)
  2. washThe combined organic fractions were washed with brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-984d60de30594a708b75f571cc77d440
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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