(2-{4-[3-({1-[bis-(4-chlorophenyl)methyl]azetidin-3-ylidene}methanesulfonylmethyl)phenyl]piperazin-1-yl}-2-oxoethyl)-N-methylcarbamic acid tert-butyl ester → HCID 69635723, compound

HRID 1058831Notes

Reaction equation

HRID 1058831 reaction equation
C(O[C:6](=O)[N:7]([CH2:9][C:10]([N:12]1[CH2:17][CH2:16][N:15]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([CH2:24][S:25]([CH:28]=[C:29]3[CH2:32][N:31]([CH:33]([C:41]4[CH:46]=[CH:45][C:44]([Cl:47])=[CH:43][CH:42]=4)[C:34]4[CH:39]=[CH:38][C:37]([Cl:40])=[CH:36][CH:35]=4)[CH2:30]3)(=[O:27])=[O:26])[CH:19]=2)[CH2:14][CH2:13]1)=[O:11])C)(C)(C)C>C(O)=O>[Cl:40][C:37]1[CH:36]=[CH:35][C:34]([CH:33]([C:41]2[CH:42]=[CH:43][C:44]([Cl:47])=[CH:45][CH:46]=2)[N:31]2[CH2:30][C:29](=[CH:28][S:25]([CH2:24][C:20]3[CH:19]=[C:18]([N:15]4[CH2:14][CH2:13][N:12]([C:10](=[O:11])[CH2:9][NH:7][CH3:6])[CH2:17][CH2:16]4)[CH:23]=[CH:22][CH:21]=3)(=[O:27])=[O:26])[CH2:32]2)=[CH:39][CH:38]=1

Participants

3

Reactant 1

HCID 69635644(2-{4-[3-({1-[bis-(4-chlorophenyl)methyl]azetidin-3-ylidene}methanesulfonylmethyl)phenyl]piperazin-1-yl}-2-oxoethyl)-N-methylcarbamic acid tert-butyl ester

Product 1

HCID 69635723HCID 69635723, compoundYield 83.3%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

A solution of 81 mg of (2-{4-[3-({1-[bis-(4-chlorophenyl)methyl]azetidin-3-ylidene}methanesulfonylmethyl)phenyl]piperazin-1-yl }-2-oxoethyl)-N-methylcarbamic acid tert-butyl ester in 2.5 cm3 of formic acid is stirred for 1 hour at a temperature close to 45° C. The reaction mixture is concentrated to dryness under reduced pressure (5 kPa) at a temperature close to 30° C., taken up in 10 cm3 of ethyl acetate and alkalinized with 10 cm3 of a saturated aqueous sodium bicarbonate solution. After separating after settling out, the organic phase is washed with 10 cm3 of water, dried over magnesium sulfate, filtered and concentrated to dryness under reduced pressure (1 kPa) at a temperature close to 40° C. 58 mg of 1-{4-[3-({1-[bis-(4-chlorophenyl)methyl]azetidin-3-ylidene}methanesulfonylmethyl)phenyl]piperazin-1-yl}-2-methylaminoethanone are thus obtained in the form of a beige lacquer [1H NMR spectrum (300 MHz, CDCl3), δ in ppm): from 1.95 to 2.15 (broad unresolved complex, 1H), 2.51 (broad s, 3H), 2.77 (s, 3H), from 3.10 to 3.30 (mt, 4H), 3.49 (broad s, 2H), 3.58 (mt, 2H), from 3.75 to 3.90 (mt, 4H), 4.33 (mt, 2H), 4.49 (s, 1H), 6.83 (broad d, J=8 Hz, 1H), 6.90 (dd, J=8 and 2 Hz, 1H), 7.00 (mt, 1H), from 7.20 to 7.40 (mt, 9H)].

Workup

  1. customclose to 45° C
  2. concentrationThe reaction mixture is concentrated to dryness under reduced pressure (5 kPa) at a temperature
  3. customclose to 30° C.
  4. customAfter separating
  5. washthe organic phase is washed with 10 cm3 of water
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated to dryness under reduced pressure (1 kPa) at a temperature
  9. customclose to 40° C

Sources & evidence

ORD record
ord-bdaaa9f595eb46d39e2019de512d3a7e
Source dataset
uspto-grants-2003_02
Patent number
US06518264B2

Reaction notes

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