N-methyl-2-pyrrolidone → HCID 67507564, compound

HRID 1791911Notes

Reaction equation

HRID 1791911 reaction equation
Cl.Cl.Cl.[N+:4]([C:7]1[CH:12]=[CH:11][C:10]([N:13]2[CH2:18][CH2:17][CH:16]([NH:19][C@@H:20]3[CH2:24][NH:23][C@H:22]([C:25]([N:27]4[CH2:31][CH2:30][S:29][CH2:28]4)=[O:26])[CH2:21]3)[CH2:15][CH2:14]2)=[CH:9][CH:8]=1)([O-:6])=[O:5].[C:32]([C:34]1[CH:41]=[CH:40][C:37]([CH2:38]Br)=[CH:36][CH:35]=1)#[N:33].C(N([CH:48]([CH3:50])[CH3:49])CC)(C)C.[C:51](=[O:54])([O-])[OH:52].[Na+].[CH3:56]N1CCCC1=O>>[C:48]([O:52][C:51]([N:23]1[CH2:24][C@@H:20]([N:19]([CH2:38][C:37]2[CH:40]=[CH:41][C:34]([C:32]#[N:33])=[CH:35][CH:36]=2)[CH:16]2[CH2:15][CH2:14][N:13]([C:10]3[CH:11]=[CH:12][C:7]([N+:4]([O-:6])=[O:5])=[CH:8][CH:9]=3)[CH2:18][CH2:17]2)[CH2:21][C@H:22]1[C:25]([N:27]1[CH2:31][CH2:30][S:29][CH2:28]1)=[O:26])=[O:54])([CH3:50])([CH3:56])[CH3:49]

Participants

6

Reactant 5

HCID 13387N-methyl-2-pyrrolidoneHCID 81531DiisopropylethylamineHCID 869964-(Bromomethyl)benzonitrileHCID 516892Sodium BicarbonateHCID 67506523HCID 67506523, compound

Product 1

HCID 67507564HCID 67507564, compound

Conditions

Temperature
80 °C

Procedure

The product (1.01 g) of Example 156 (3) was dissolved in N-methyl-2-pyrrolidone (6 mL), and 4-cyanobenzyl bromide (0.392 g) and diisopropylethylamine (1.05 mL) were added thereto. The mixture was stirred at 80° C. for 8 hr with heating. The reaction mixture was added to saturated aqueous sodium hydrogencarbonate solution and the mixture was extracted with ethyl acetate. The extract was dried and the solvent was evaporated under reduced pressure. The residue was purified by silica gel chromatography to give 3-{(2S,4S)-1-tert-butoxycarbonyl-4-{N-(4-cyanophenylmethyl)-N-[1-(4-nitrophenyl)-4-piperidinyl]amino}-2-pyrrolidinylcarbonyl}-1,3-thiazolidine (0.685 g) as a yellow oil.

Workup

  1. temperaturewith heating
  2. extractionthe mixture was extracted with ethyl acetate
  3. customThe extract was dried
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-1ed59873ae734812b5b5a08a76fbb05e
Source dataset
uspto-grants-2006_07
Patent number
US07074794B2

Reaction notes

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