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Triethylamine → HCID 10670821, compound

HRID 619839
Notes
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Reaction equation

HRID 619839 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].[CH3:17][O:18][C:19]1[CH:28]=[C:27]2[C:22]([CH:23]=[CH:24][C:25]([S:29](Cl)(=[O:31])=[O:30])=[CH:26]2)=[CH:21][CH:20]=1.C(N(CC)CC)C>C(Cl)Cl.CCOC(C)=O.O>[C:14]([C:11]1[S:12][CH:13]=[C:9]([CH2:8][N:5]2[CH2:6][CH2:7][C@H:3]([NH:2][S:29]([C:25]3[CH:24]=[CH:23][C:22]4[C:27](=[CH:28][C:19]([O:18][CH3:17])=[CH:20][CH:21]=4)[CH:26]=3)(=[O:31])=[O:30])[C:4]2=[O:16])[CH:10]=1)#[N:15]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 105152667-methoxynaphthalene-2-sulfonyl ChlorideHCID 193510444-(3-Amino-2-oxopyrrolidine-1-ylmethyl)thiophene-2-carbonitrile hydrochloride

Product 1

HCID 10670821HCID 10670821, compoundYield 67.8%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent
HCID 6344
Dichloromethane
Solvent
HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-(3-Amino-2-oxopyrrolidine-1-ylmethyl)thiophene-2-carbonitrile hydrochloride (0.43 g, 1.8 mmol), prepared as in EXAMPLE 122, in 10 mL of CH2Cl2 is added 7-methoxynaphthalene-2-sulfonyl chloride (0.51 g, 2 mmol) and triethyl amine (0.55 g, 5.4 mmol). After 16 hours, the solution is diluted with EtOAc and H2O. The layers are separated. The organic layer is washed with 1 N HCl, sat. NaHCO3 and sat. NaCl. The organic layer is dried over MgSO4, filtered and concentrated. The crude product is purified by column chromatography eluting with gradient of 10% EtOAc/CH2Cl2 to 20% EtOAc/CH2Cl2 to afford the title compound (0.50 g, 1.22 mmol) as a white solid.

Workup

  1. customThe layers are separated
  2. washThe organic layer is washed with 1 N HCl, sat. NaHCO3 and sat. NaCl
  3. dry with materialThe organic layer is dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product is purified by column chromatography
  7. washeluting with gradient of 10% EtOAc/CH2Cl2 to 20% EtOAc/CH2Cl2

Sources & evidence

ORD record
ord-09c4ad70860a42c4af33fa23e3e99fd8
Source dataset
uspto-grants-1999_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05958918

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes