1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → HCID 68545320, compound

HRID 1446756Notes

Reaction equation

HRID 1446756 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=O)=[C:4]([F:12])[CH:3]=1.O.OC1C2N=NNC=2C=CC=1.Cl.CN(C)CCCN=C=NCC.[C:36]([O:40][C:41](=[O:53])[NH:42][C:43]([C:46]1[CH:51]=[CH:50][CH:49]=[C:48]([NH2:52])[CH:47]=1)([CH3:45])[CH3:44])([CH3:39])([CH3:38])[CH3:37]>CC=C(C)C.ClCCl.C(Cl)(Cl)Cl>[C:36]([O:40][C:41](=[O:53])[NH:42][C:43]([C:46]1[CH:51]=[CH:50][CH:49]=[C:48]([NH:52][C:9](=[O:11])[CH2:8][C:5]2[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][C:4]=2[F:12])[CH:47]=1)([CH3:45])[CH3:44])([CH3:37])([CH3:38])[CH3:39]

Participants

8

Reactant 4

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 140537922-(4-Bromo-2-fluorophenyl)acetic acidHCID 229810903-[2-(Boc-amino)-2-propyl]anilineHCID 178526939HCID 178526939, compound

Product 1

HCID 68545320HCID 68545320, compoundYield 71%

Reagents, catalysts & solvents 3

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolventHCID 105532-Methyl-2-buteneSolvent

Procedure

Dissolve (4-bromo-2-fluoro-phenyl)acetic acid (1.49 g, 6.39 mmol) in 25 mL amylene-stabilized chloroform and add hydroxybenzotriazole hydrate (0.95 g, 7.03 mmol), to give a slurry. Add 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (1.47 g, 7.67 mmol) and stir the resulting clear solution at room temperature for 15 minutes. Add [1-(3-amino-phenyl)-1-methyl-ethyl]-carbamic acid tert-butyl ester and stir for 90 minutes at room temperature. Dilute reaction with 20 mL dichloromethane and wash with saturated NaHCO3, 1 N NaHSO4, and dilute aqueous saturated sodium chloride, then dry over MgSO4 and concentrate to give a brittle tan foam. Purify the foam on a 120 g silica cartridge with 100% CH2Cl2 for 5 minutes followed by a gradient of 0→10% EtOAc in CH2Cl2 over 40 minutes. Concentrate and dry clean fractions to provide 2.11 g (71%) of the title compound as a brittle white foam. LCMS (ES) m/z 463/465 (M−1).

Workup

  1. customto give a slurry
  2. additionDilute
  3. washwash with saturated NaHCO3, 1 N NaHSO4, and dilute aqueous saturated sodium chloride
  4. dry with materialdry over MgSO4
  5. concentrationconcentrate
  6. customto give a brittle tan foam
  7. customPurify the foam on a 120 g silica cartridge with 100% CH2Cl2 for 5 minutes
  8. concentrationConcentrate
  9. customdry clean fractions

Sources & evidence

ORD record
ord-d9332660bb8c4f3c81fd188770a5ece8
Source dataset
uspto-grants-2010_02
Patent number
US07666879B2

Reaction notes

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