Triethylamine → HCID 68506750, compound

HRID 1715435Notes

Reaction equation

HRID 1715435 reaction equation
[C:1]([O:5][C:6](=[O:20])[N:7]([CH2:10][C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[C:13]([CH:18]=O)[CH:12]=1)[CH2:8][CH3:9])([CH3:4])([CH3:3])[CH3:2].[CH:21]1([NH2:24])[CH2:23][CH2:22]1.CCN(CC)CC.[BH4-].[Na+].C([O-])(O)=O.[Na+]>CO>[C:1]([O:5][C:6](=[O:20])[N:7]([CH2:10][C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[C:13]([CH2:18][NH:24][CH:21]2[CH2:23][CH2:22]2)[CH:12]=1)[CH2:8][CH3:9])([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 69828CyclopropylamineHCID 516892Sodium BicarbonateHCID 4311764Sodium borohydrideHCID 86622968HCID 86622968, compound

Product 1

HCID 68506750HCID 68506750, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of (4-chloro-3-formyl-benzyl)-ethyl-carbamic acid tert-butyl ester (240 mg, 0.806 mmol), cyclopropylamine (0.085 mL, 1.2 mmol) and Et3N (0.169 mL, 1.21 mmol) in MeOH (2.7 mL) was heated to reflux for 4 h. The mixture was allowed to cool to rt, and NaBH4 (76.2 mg, 2.01 mmol) was added. The mixture was stirred for 1 h at rt, and aq. sat. NaHCO3 was added. The mixture was extracted several times with EtOAc. The combined org. extracts were dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Purification of the crude by FC (MeOH/CH2Cl2 1:49) yielded the title compound (125 mg, 46%). LC-MS: tR=0.78 min; ES+: 380.20.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 4 h
  3. extractionThe mixture was extracted several times with EtOAc
  4. dry with materialextracts were dried over MgSO4
  5. filtrationfiltered
  6. customthe solvents were removed under reduced pressure
  7. customPurification of the crude by FC (MeOH/CH2Cl2 1:49)

Sources & evidence

ORD record
ord-c79e0fcda74543d4b645c1219e339f08
Source dataset
uspto-grants-2010_09
Patent number
US07799805B2

Reaction notes

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