Pyrrolidine → HCID 86583542, compound

HRID 1790562Notes

Reaction equation

HRID 1790562 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 5ml 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-ca099d0d7c624a328aad0b0607c66f7b
Source dataset
uspto-grants-2006_07
Patent number
US07071212B2

Reaction notes

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