Tert-Butylamine → HCID 43132548, compound

HRID 1376104Notes

Reaction equation

HRID 1376104 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:8]([F:11])=[CH:7][C:3]=1[C:4]([OH:6])=O.ON1C(=O)CCC1=O.CN(C1C=CC=CN=1)C.C1(N=C=NC2CCCCC2)CCCCC1.[C:44]([NH2:48])([CH3:47])([CH3:46])[CH3:45]>ClCCl>[NH2:1][C:2]1[CH:10]=[CH:9][C:8]([F:11])=[CH:7][C:3]=1[C:4]([NH:48][C:44]([CH3:47])([CH3:46])[CH3:45])=[O:6]

Participants

7

Reactant 5

HCID 6385Tert-ButylamineHCID 10868DicyclohexylcarbodiimideHCID 218852-DimethylaminopyridineHCID 80170N-HydroxysuccinimideHCID 1014122-Amino-5-fluorobenzoic acid

Product 1

HCID 43132548HCID 43132548, compoundYield 73.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Stir and cool to 0° C. a solution of 2-amino-5-fluorobenzoic acid (7.75 g, 50 mmol), N-hydroxysuccinimide (6.9 g, 60 mmol) and dimethylaminopyridine (1.0 g) in dichloromethane (200 mL). Add, dropwise, a 1M solution of dicyclohexylcarbodiimide in dichloromethane (60 mL, 60 mmol), and stir at 0° C. for 1H. Add tert-butyl amine (20 mL, 190.3 mmol) by syringe and stir at 0° C. for 3 h and then at ambient temperature overnight. Pour onto a pad of silica gel and elute with 5% ethyl acetate/dichloromethane. Combine like fractions and concentrate to obtain a crude solid. Triturate the solid with heptane and filter to obtain 7.7 g (73%) of the title compound: MS 211(M+H), m.p. 77–78° C.

Workup

  1. additionAdd
  2. customat ambient temperature
  3. customovernight
  4. additionPour onto a pad of silica gel
  5. washelute with 5% ethyl acetate/dichloromethane
  6. concentrationconcentrate
  7. customto obtain a crude solid
  8. customTriturate the solid with heptane
  9. filtrationfilter

Sources & evidence

ORD record
ord-c6ae5f54713d4bcf84e1ebc03d7367c2
Source dataset
uspto-grants-2007_01
Patent number
US07169925B2

Reaction notes

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