Tetrahydrofuran → HCID 66864196, compound

HRID 2093429Notes

Reaction equation

HRID 2093429 reaction equation
ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.[Cl:23][C:24]1[CH:29]=[CH:28][C:27]([CH:30]([C:49]2[CH:54]=[CH:53][C:52]([Cl:55])=[CH:51][CH:50]=2)[N:31]2[CH2:34][CH:33]([CH2:35][S:36]([NH:39][C:40]3[CH:48]=[CH:47][CH:46]=[CH:45][C:41]=3C(O)=O)(=[O:38])=[O:37])[CH2:32]2)=[CH:26][CH:25]=1.Cl.[NH2:57][C@@H:58]([C:60]([NH2:62])=[O:61])[CH3:59].[O:63]1CCC[CH2:64]1>ClCCl.C(N(CC)CC)C>[Cl:55][C:52]1[CH:51]=[CH:50][C:49]([CH:30]([C:27]2[CH:28]=[CH:29][C:24]([Cl:23])=[CH:25][CH:26]=2)[N:31]2[CH2:32][CH:33]([CH2:35][S:36]([NH:39][C:40]3[CH:48]=[C:47]([CH:46]=[CH:45][CH:41]=3)[C:64]([NH:57][C@@H:58]([C:60](=[O:61])[NH2:62])[CH3:59])=[O:63])(=[O:38])=[O:37])[CH2:34]2)=[CH:54][CH:53]=1

Participants

8

Reactant 5

HCID 8028TetrahydrofuranHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 2775814(2R)-2-Aminopropanamide hydrochlorideHCID 86649696HCID 86649696, compound

Product 1

HCID 66864196HCID 66864196, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
20 °C

Procedure

67 mg of 1-hydroxybenzotriazole, 0.4 cm3 of triethylamine and 228 mg of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride are added successively to a solution of 500 mg of 3-({1-[bis(4-chlorophenyl)methyl]azetidin-3-yl}methanesulphonylaminobenzoic acid and 150 mg of D-alaninamide hydrochloride in 20 cm3 of tetrahydrofuran. The reaction mixture is left stirring overnight at a temperature in the region of 20° C. After concentration of the reaction medium to dryness under reduced pressure, the yellowish-white powder obtained is dissolved with dichloromethane. The organic phase is washed with water. After separation by settling out, the aqueous phase is again extracted with dichloromethane. The reaction crude obtained after concentration of the organic phases to dryness under reduced pressure is purified by flash chromatography on a Merck 30 g silica cartridge (elution gradient: 100/0 to 95/5 dichloromethane/methanol). After concentration of the fractions under reduced pressure, a product is obtained which is washed with diethyl ether and oven-dried under vacuum. 220 mg of 3-({1-[bis(4-chlorophenyl)methyl]azetidin-3-yl}methanesulphonylamino)-N—((R)-1-carbamoylethyl)benzamide are thus obtained in the form of white crystals.

Workup

  1. waitThe reaction mixture is left
  2. customAfter concentration of the reaction medium to dryness under reduced pressure, the yellowish-white powder obtained
  3. washThe organic phase is washed with water
  4. customAfter separation
  5. extractionthe aqueous phase is again extracted with dichloromethane
  6. customThe reaction crude
  7. customobtained after concentration of the organic phases to dryness under reduced pressure
  8. customis purified by flash chromatography on a Merck 30 g silica cartridge (elution gradient: 100/0 to 95/5 dichloromethane/methanol)
  9. customAfter concentration of the fractions under reduced pressure, a product is obtained which
  10. washis washed with diethyl ether
  11. customoven-dried under vacuum

Sources & evidence

ORD record
ord-8fc5298147584856aa006472e3dda0de
Source dataset
uspto-grants-2013_05
Patent number
US08445478B2

Reaction notes

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