1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 11705243, compound

HRID 1467899Notes

Reaction equation

HRID 1467899 reaction equation
[CH:1]1([N:4]([CH:18]2[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]2)[S:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:17])([F:16])[F:15])[CH:9]=2)(=[O:7])=[O:6])[CH2:3][CH2:2]1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.C(OC([NH:52][C:53]1([C:58](O)=[O:59])[CH2:57][CH2:56][CH2:55][CH2:54]1)=O)(C)(C)C>CN(C=O)C>[NH2:52][C:53]1([C:58]([N:21]2[CH2:22][CH2:23][CH:18]([N:4]([CH:1]3[CH2:3][CH2:2]3)[S:5]([C:8]3[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:17])([F:15])[F:16])[CH:9]=3)(=[O:6])=[O:7])[CH2:19][CH2:20]2)=[O:59])[CH2:57][CH2:56][CH2:55][CH2:54]1

Participants

6

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 27346451-tert-Butoxycarbonylaminocyclopentanecarboxylic acidHCID 2773944N-Cyclopropyl-N-piperidin-4-yl-3-(trifluoromethyl)benzenesulfonamide

Product 1

HCID 11705243HCID 11705243, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N-Cyclopropyl-N-piperidin-4-yl-3-trifluoromethyl-benzenesulfonamide (14) (0.400 g, 1.15 mmol) was taken up in 10 mL of dry DMF. To this mixture, HOBt (0.154 g, 1.15 mmol), EDCI (0.218 g, 1.15 mmol), and 1-tert-butoxycarbonylaminocyclopentane-1-carboxylic acid (0.263 g, 1.15 mmol) were added. The mixture was allowed to stir at room temperature for 16 hours. The reaction mixture was concentrated to dryness under reduced pressure and the crude material was chromatographed on silica eluting with 25% ethyl acetate/hexane. The combined product fractions were concentrated to dryness and the pure BOC-protected material was deprotected in 40 mL of ethyl acetate/concentrated HCl (19:1). The solvent was removed leaving a white solid material. This material was triturated with diethyl ether and vacuum filtered affording the desired sulfonamide (48) as the HCl-salt. LC: 97%. MS (e/z): 460 (M+H+). 1H NMR of salt (CD3OD): δ 8.02 (m, 2H), 7.83 (d, 1H, J=7.86 Hz), 7.66 (t, 1H, J=7.86 Hz), 4.01 (m, 2.5H), 2.80 (bs, 1.5H), 2.11 (m, 2H), 1.7-2.0 (m, 10H), 1.51 (m, 2H), 0.60 (m, 2H), 0.50 (m, 2H).

Workup

  1. concentrationThe reaction mixture was concentrated to dryness under reduced pressure
  2. customthe crude material was chromatographed on silica eluting with 25% ethyl acetate/hexane
  3. concentrationThe combined product fractions were concentrated to dryness
  4. customThe solvent was removed
  5. customleaving a white solid material
  6. customThis material was triturated with diethyl ether and vacuum
  7. filtrationfiltered

Sources & evidence

ORD record
ord-a6b4c11b1ca949709c5d1e604af6ee94
Source dataset
uspto-grants-2015_04
Patent number
US09000174B2

Reaction notes

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