Dichloromethane → HCID 66864152, compound

HRID 2093427Notes

Reaction equation

HRID 2093427 reaction equation
ON1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2N=N1.[ClH:11].[CH3:12][N:13]([CH3:22])[CH2:14][CH2:15][CH2:16]N=C=NCC.ClC1C=CC(C(C2C=CC(Cl)=CC=2)N2CC([N:35]([S:45](C)(=[O:47])=[O:46])[C:36]3[CH:37]=[C:38]([CH:42]=[CH:43][CH:44]=3)[C:39]([OH:41])=O)C2)=CC=1.Cl.[NH2:57][C@H:58]([C:60]([NH2:62])=[O:61])[CH3:59].Cl[CH2:64][Cl:65]>O1CCCC1.C(N(CC)CC)C>[Cl:11][C:5]1[CH:10]=[CH:9][C:8]([CH:22]([C:5]2[CH:10]=[CH:9][C:64]([Cl:65])=[CH:7][CH:6]=2)[N:13]2[CH2:12][CH:15]([CH2:16][S:45]([NH:35][C:36]3[CH:37]=[C:38]([CH:42]=[CH:43][CH:44]=3)[C:39]([NH:57][C@H:58]([C:60](=[O:61])[NH2:62])[CH3:59])=[O:41])(=[O:46])=[O:47])[CH2:14]2)=[CH:7][CH:6]=1

Participants

8

Reactant 5

HCID 6344DichloromethaneHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 2775816(S)-2-aminopropanamide hydrochlorideHCID 23117283HCID 23117283, compound

Product 1

HCID 66864152HCID 66864152, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 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}(methanesulphonyl)amino]benzoic acid and 150 mg of L-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 in 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 white powder is obtained, which is washed with ethyl ether and oven-dried under vacuum. 430 mg of 3-({1-[bis(4-chlorophenyl)methyl]azetidin-3-yl}methanesulphonylamino)-N—((S)-1-carbamoylethyl)benzamide are thus obtained in the form of a white solid.

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 white powder is obtained
  10. washwhich is washed with ethyl ether
  11. customoven-dried under vacuum

Sources & evidence

ORD record
ord-30cf2c2fa727478b8195da52cfa73fdd
Source dataset
uspto-grants-2013_05
Patent number
US08445478B2

Reaction notes

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