Pyrrolidine → HCID 86583542, compound

HRID 1841733Notes

Reaction equation

HRID 1841733 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([NH:9][CH:10]([C:16]2[CH:21]=[C:20]([C:22]#[C:23][Si:24]([CH3:27])([CH3:26])[CH3:25])[CH:19]=[C:18]([CH2:28]O)[CH:17]=2)[C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:5][CH:4]=1)#[N:2].CS(Cl)(=O)=O.[NH:35]1[CH2:39][CH2:38][CH2:37][CH2:36]1>C(Cl)Cl.C(N(CC)CC)C.C1COCC1>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([NH:9][CH:10]([C:16]2[CH:21]=[C:20]([C:22]#[C:23][Si:24]([CH3:26])([CH3:27])[CH3:25])[CH:19]=[C:18]([CH2:28][N:35]3[CH2:39][CH2:38][CH2:37][CH2:36]3)[CH:17]=2)[C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:7][CH:8]=1)#[N:2]

Participants

7

Reactant 3

HCID 31268PyrrolidineHCID 31297Methanesulfonyl chlorideHCID 86583540HCID 86583540, compound

Product 1

HCID 86583542HCID 86583542, compound

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolvent2×

Procedure

398 mg of the ethyl (RS)-(4-cyano-phenylamino)-(3-hydroxymethyl-5-trimethylsilanylethynyl-phenyl)-acetate described in Example 156.3 were dissolved in 6 ml of CH2Cl2 g and 0.41 ml of triethylamine followed by 0.1 ml of methanesulphonyl chloride were added dropwise at 0° C. The mixture was stirred overnight and an intermediate was then isolated by extraction. This was taken up in 5 ml of THF and stirred together with 0.41 ml of triethylamine and 0.32 ml of pyrrolidine. By repeat extraction there was obtained a crude product, which was purified by column chromatography (cyclohexan/ethyl acetate). There were obtained 130 mg of ethyl (RS)-(4-cyano-phenylamino)-(3-pyrrolidin-1-ylmethyl-5-trimethylsilanylethynyl-phenyl)-acetate as a light brown solid; MS: 460 ([M]+).

Workup

  1. additionwere added dropwise at 0° C
  2. customan intermediate was then isolated by extraction
  3. extractionBy repeat extraction
  4. customthere was obtained a crude product, which
  5. customwas purified by column chromatography (cyclohexan/ethyl acetate)

Sources & evidence

ORD record
ord-566a77f5dccc4452aa0bab41edd843e0
Source dataset
uspto-grants-2004_01
Patent number
US06683215B2

Reaction notes

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