1-Hydroxybenzotriazole → HCID 66864043, compound

HRID 2093430Notes

Reaction equation

HRID 2093430 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:41]=[C:42]([CH:46]=[CH:47][CH:48]=3)[C:43]([OH:45])=O)(=[O:38])=[O:37])[CH2:32]2)=[CH:26][CH:25]=1.Cl.[NH2:57][CH2:58][C:59]([N:61]1[CH2:66][CH2:65][O:64][CH2:63][CH2:62]1)=[O:60]>O1CCCC1.ClCCl.C(N(CC)CC)C>[Cl:23][C:24]1[CH:25]=[CH:26][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:41]=[C:42]([CH:46]=[CH:47][CH:48]=3)[C:43]([NH:57][CH2:58][C:59]([N:61]3[CH2:66][CH2:65][O:64][CH2:63][CH2:62]3)=[O:60])=[O:45])(=[O:37])=[O:38])[CH2:32]2)=[CH:28][CH:29]=1

Participants

8

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 122918142-Amino-1-(morpholin-4-yl)ethan-1-one--hydrogen chloride (1/1)HCID 66864534HCID 66864534, compound

Product 1

HCID 66864043HCID 66864043, compound

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
20 °C

Procedure

67 mg of 1-hydroxybenzotriazole, 0.14 cm3 of triethylamine and 270 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}methanesulphonylamino)benzoic acid and 215 mg of 2-amino-1-morpholin-4-ylethanone hydrochloride in 15 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 residue obtained is taken up with dichloromethane. The organic phase is washed with water, dried, and concentrated to dryness under reduced pressure, to give a reaction crude which 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 foam is obtained which crystallizes after trituration with diethyl ether. After filtration and drying using a vane pump, 470 mg of 3-({1-[bis(4-chlorophenyl)methyl]azetidin-3-yl}methanesulphonylamino)-N-(2-morpholin-4-yl-2-oxoethyl)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 residue obtained
  3. washThe organic phase is washed with water
  4. customdried
  5. concentrationconcentrated to dryness under reduced pressure
  6. customto give
  7. customa reaction crude which
  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 foam is obtained which
  10. customcrystallizes after trituration with diethyl ether
  11. filtrationAfter filtration
  12. customdrying
  13. customare thus obtained in the form of white crystals

Sources & evidence

ORD record
ord-9b24d917cc614ef9928ca4e68d8cf6f7
Source dataset
uspto-grants-2013_05
Patent number
US08445478B2

Reaction notes

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