Cyclopropylamine → HCID 11503850, compound

HRID 851984Notes

Reaction equation

HRID 851984 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]([CH2:20][C:21]2[CH:29]=[CH:28][C:24]([C:25](O)=[O:26])=[CH:23][CH:22]=2)[CH:12]2[CH2:18][CH2:17][CH2:16][CH2:15][NH:14][C:13]2=[O:19])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[B-](F)(F)(F)F.CN(C(O[N:43]1[C:48](=O)[CH:47]=[CH:46]C=C1)=[N+](C)C)C.CCN(C(C)C)C(C)C.C1(N)CC1>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([N:11]([CH2:20][C:21]2[CH:22]=[CH:23][C:24]([C:25]([NH:43][CH:48]3[CH2:46][CH2:47]3)=[O:26])=[CH:28][CH:29]=2)[CH:12]2[CH2:18][CH2:17][CH2:16][CH2:15][NH:14][C:13]2=[O:19])(=[O:10])=[O:9])=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 69828CyclopropylamineHCID 81531Diisopropylethylamine2×HCID 2733204O-(2-Oxo-1(2H)-pyridyl)-N,N,N',N'-tetramethyluronium TetrafluoroborateHCID 18455048HCID 18455048, compound

Product 1

HCID 11503850HCID 11503850, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

rac-4-{[(4-Chloro-benzenesulfonyl)-(2-oxo-azepan-3-yl)-amino]-methyl}-benzoic acid (0.70 g, 1.6 mmol) was dissolved in DMF and activated with the coupling reagent TPTU (0.48 g, 1.6 mmol) and Hünig's base (0.55 ml, 3.2 mmol) for 2 min. ⅛ of this activated mixture was delivered to a reaction tube on a parallel synthesizer containing cyclopropylamine (0.013 g, 0.22 mmol) and a further amount of Hünig's base (0.04 ml, 0.22 mmol) in DMF (3 ml). The reaction mixture was shaken for 2 h, concentrated under reduced pressure and purified directly using preparative RP(C18) chromatography: lyophilisate 40 mg; MS: m/e=476.1 (MH+), 493.1 (MNH4+).

Workup

  1. customwas delivered to a reaction tube on a parallel synthesizer
  2. concentrationconcentrated under reduced pressure
  3. custompurified directly

Sources & evidence

ORD record
ord-e75235600175414f915be06d4e3e1441
Source dataset
uspto-grants-2007_08
Patent number
US07253158B2

Reaction notes

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