Ethyl Acetate → HCID 20579057, compound

HRID 1267095Notes

Reaction equation

HRID 1267095 reaction equation
[NH2:1][CH2:2][C@H:3]1[CH2:7][C@@H:6]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[C:11]([Cl:16])[CH:10]=2)[CH2:5][N:4]1[CH3:17].C1(C2C=NC(CC(O)=[S:32])=NC=2)C=CC=CC=1.C[CH2:35][N:36]=[C:37]=[N:38][CH2:39][CH2:40][CH2:41]N(C)C.C1[CH:46]=[CH:47][C:48]2N(O)N=N[C:49]=2[CH:50]=1.[CH3:55][CH2:56][O:57]C(C)=O>C(Cl)Cl>[ClH:15].[Cl:16][C:11]1[CH:10]=[C:9]([CH:14]=[CH:13][C:12]=1[Cl:15])[CH2:8][C@H:6]1[CH2:5][N:4]([CH3:17])[C@@H:3]([CH2:2][NH:1][C:56](=[O:57])[CH2:55][S:32][C:37]2[N:36]=[CH:35][C:40]([C:41]3[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=3)=[CH:39][N:38]=2)[CH2:7]1

Participants

7

Reactant 5

HCID 8857Ethyl AcetateHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 60209511HCID 60209511, compoundHCID 178526165HCID 178526165, compound

Product 1

HCID 20579057HCID 20579057, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a CH2Cl2 solution of (2R,4R)-2-aminomethyl-4-(3,4-dichlorobenzyl)-1-methyl-pyrrolidine (prepared as described in example 4.4) (40 mg, 0.15 mmol) was added 5-phenylpyrimidin-2-ylthioacetic acid (40 mg, 0.16 mmol), EDCI (36 mg, 0.19 mmol), and HOBT (2 mg, 0.015 mmol) The reaction mixture was stirred for 16 h at room temperature and then diluted with EtOAc and washed with aqueous NaHCO3. The organic layer was dried over MgSO4, filtered, and concentrated. Flash chromatography (95% CH2Cl2/5% MeOH) provided N-(2R,4R)-[4-(3,4-dichlorobenzyl)-1-methylpyrrolidin-2-ylmethyl]-2-[5-(phenyl)pyrimidin-2-ylsulfanyl]acetamide hydrochloride (47 mg, 0.098 mmol) mass spectrum 502 (MH+).

Workup

  1. washwashed with aqueous NaHCO3
  2. dry with materialThe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-804fe9b8e3c9446aa0ef2696553103c4
Source dataset
uspto-grants-2003_04
Patent number
US06552028B2

Reaction notes

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