Triethylamine → 4-{3-(S)-[(4-(6-Nitro-2-chlorophenoxy)benzenesulfonyl)amino]-2-oxopyrrolidin-1-ylmethyl}thiophene-2-carbononitrile

HRID 619865Notes

Reaction equation

HRID 619865 reaction equation
Cl.[NH2:2][CH:3]1[CH2:7][CH2:6][N:5]([CH2:8][C:9]2[CH:10]=[C:11]([C:14]#[N:15])[S:12][CH:13]=2)[C:4]1=[O:16].[N+:17]([C:20]1[C:25]([O:26][C:27]2[CH:32]=[CH:31][C:30]([S:33](Cl)(=[O:35])=[O:34])=[CH:29][CH:28]=2)=[C:24]([Cl:37])[CH:23]=[CH:22][CH:21]=1)([O-:19])=[O:18].C(N(CC)CC)C>C(Cl)Cl.Cl>[N+:17]([C:20]1[C:25]([O:26][C:27]2[CH:32]=[CH:31][C:30]([S:33]([NH:2][C@H:3]3[CH2:7][CH2:6][N:5]([CH2:8][C:9]4[CH:10]=[C:11]([C:14]#[N:15])[S:12][CH:13]=4)[C:4]3=[O:16])(=[O:34])=[O:35])=[CH:29][CH:28]=2)=[C:24]([Cl:37])[CH:23]=[CH:22][CH:21]=1)([O-:19])=[O:18]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 27742764-(2-Chloro-6-nitrophenoxy)benzene-1-sulfonyl chlorideHCID 193510444-(3-Amino-2-oxopyrrolidine-1-ylmethyl)thiophene-2-carbonitrile hydrochloride

Product 1

HCID 673655054-{3-(S)-[(4-(6-Nitro-2-chlorophenoxy)benzenesulfonyl)amino]-2-oxopyrrolidin-1-ylmethyl}thiophene-2-carbononitrileYield 96.4%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 6344DichloromethaneSolvent

Procedure

4-{3-(S)-[(4-(6-Nitro-2-chlorophenoxy)benzenesulfonyl)amino]-2-oxopyrrolidin-1-ylmethyl}thiophene-2-carbononitrile is prepared as described in EXAMPLE 125, Part C from of 4-(3-Amino-2-oxopyrrolidine-1-ylmethyl)thiophene-2-carbonitrile hydrochloride (0.36 g, 1.4 mmol), and 4-(6-Nitro-2-chlorophenoxy)-benzenesulfonyl chloride (0.63 g, 1.8 mmol) and triethyl amine (0.57 g, 5.7 mmol). After 18 hours, the solution is diluted with CH2Cl2 and 0.5 N HCl. The layers are separated; the organic layer is dried over NA2SO4, filtered and concentrated. The crude product is triturated with ether to afford the title compound (0.72 g, 1.35 mmol) as a white foam.

Workup

  1. custom4-{3-(S)-[(4-(6-Nitro-2-chlorophenoxy)benzenesulfonyl)amino]-2-oxopyrrolidin-1-ylmethyl}thiophene-2-carbononitrile is prepared
  2. customThe layers are separated
  3. customthe organic layer is dried over NA2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product is triturated with ether

Sources & evidence

ORD record
ord-bbb8190eaaa64b73a8338fd793d9aec6
Source dataset
uspto-grants-1999_09
Patent number
US05958918

Reaction notes

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