Diisopropylcarbodiimide → HCID 21896611, compound

HRID 719097Notes

Reaction equation

HRID 719097 reaction equation
C(N=C=N[CH:7]([CH3:9])[CH3:8])(C)C.[Cl:10][C:11]1[CH:16]=[CH:15][C:14]([CH:17]([C:23]2[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=2)[N:18]2[CH2:21][CH:20]([NH2:22])[CH2:19]2)=[CH:13][CH:12]=1.[C:30]1(C)[C:31]([S:36]([CH2:39][C:40](O)=[O:41])(=[O:38])=[O:37])=[CH:32]C=C[CH:35]=1.OC1C2N=NNC=2C=CC=1>ClCCl.CN(C)C=O.CO>[Cl:10][C:11]1[CH:16]=[CH:15][C:14]([CH:17]([C:23]2[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=2)[N:18]2[CH2:19][CH:20]([NH:22][C:40](=[O:41])[CH2:39][S:36]([C:31]3[CH:32]=[CH:9][C:7]([CH3:8])=[CH:35][CH:30]=3)(=[O:38])=[O:37])[CH2:21]2)=[CH:13][CH:12]=1

Participants

8

Reactant 4

HCID 12734DiisopropylcarbodiimideHCID 218965981-[Bis(4-chlorophenyl)methyl]azetidin-3-ylamineHCID 6089029415295-73-5HCID 178418300HCID 178418300, compound

Product 1

HCID 21896611HCID 21896611, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent2×

Procedure

0.031 cm3 of diisopropylcarbodiimide, a solution of 30 mg of 1-[bis(4-chlorophenyl)-methyl]azetidin-3-ylamine in 0.5 cm3 of anhydrous dichloromethane, and 3 cm3 of anhydrous dichloromethane are added to a solution of 85.7 mg of toluenesulfonylacetic acid, 27 mg of hydroxybenzotriazole in solution in 0.5 cm3 of dimethylformamide under an inert argon atmosphere, at a temperature in the region of 23° C. After 17 hours at a temperature in the region of 23° C., the reaction mixture is loaded onto a 3-cm3 SPE cartridge containing 1 g of SCX phase preconditioned with methanol. After washing with twice 5 cm3 of methanol and then 4 cm3 of 0.1 N ammoniacal methanol, the expected product is eluted with 4 cm3 of 1 N ammoniacal methanol. The fraction containing the expected product is evaporated under an air stream at a temperature in the region of 45° C. and then dried under reduced pressure (1 mbar) at a temperature in the region of 40° C. N-{1-[bis(4-chlorophenyl)methyl]-azetidin-3-yl}-2-(toluene-4-sulfonyl)acetamide is obtained in the form of a yellow lacquer [1H NMR spectrum (500 MHz, CDCl3, δ in ppm): 2.85 (t, J=7 Hz: 2H); 3.07 (s: 3H); 3.48 (t, J=7 Hz: 2H); 4.24 (s: 1H); 4.49 (mt: 1H); 7.19 (broad d, J=6 Hz: 1H); from 7.20 to 7.40 (mt: 8H); 8.40 (s: 1H)].

Workup

  1. additioncontaining 1 g of SCX phase
  2. washAfter washing with twice 5 cm3 of methanol
  3. wash4 cm3 of 0.1 N ammoniacal methanol, the expected product is eluted with 4 cm3 of 1 N ammoniacal methanol
  4. additionThe fraction containing the expected product
  5. customis evaporated under an air stream at a temperature in the region of 45° C.
  6. customdried under reduced pressure (1 mbar) at a temperature in the region of 40° C

Sources & evidence

ORD record
ord-7c7cedeb3c474363a411e9bdf478e1d8
Source dataset
uspto-grants-2006_11
Patent number
US07132414B2

Reaction notes

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