Cyclopropylamine → 3-Bromo-4-chloro-N-cyclopropylbenzamide

HRID 1272722Notes

Reaction equation

HRID 1272722 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[Cl:11])[C:5]([OH:7])=O.CN(C(ON1N=NC2[CH:23]=[CH:24][CH:25]=[N:26]C1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C1C=CC2N(O)N=NC=2C=1.C1(N)CC1.CCN(C(C)C)C(C)C>CN(C=O)C.CO>[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[Cl:11])[C:5]([NH:26][CH:25]1[CH2:23][CH2:24]1)=[O:7]

Participants

8

Reactant 5

HCID 69828CyclopropylamineHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27355443-Bromo-4-chlorobenzoic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 184577943-Bromo-4-chloro-N-cyclopropylbenzamide

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent3×

Procedure

To a solution of 3-bromo-4-chlorobenzoic acid (120 mg) in DMF (1 ml) was added a solution of HATU (192 mg) in DMF (1 ml) and a solution of HOBT (69 mg) in DMF (1 ml). To this mixture was added cyclopropylamine (0.04 ml) and DIPEA (0.27 ml). The reaction was stirred at room temperature for 18 hours, before diluting with methanol (5 ml) and filtration through a SPE cartridge (SCX, 2 g). The filtrate was applied to a SPE cartridge (Aminopropyl, 10 g) and washed through with methanol (10 ml). The combined filtrate and washings were reduced to dryness under vacuum to give 3-bromo-4-chloro-N-cyclopropylbenzamide.

Workup

  1. washwashed through with methanol (10 ml)

Sources & evidence

ORD record
ord-ee08f686d32f4a7691d59f0f5a009837
Source dataset
uspto-grants-2007_04
Patent number
US07208629B2

Reaction notes

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