[5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-hydrazine hydrochloride → (+/-)-3-{N'-[5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-hydrazinocarbonyl}-trans-4-methyl-piperidine-1-carboxylic acid tert-butylester

HRID 1808708Notes

Reaction equation

HRID 1808708 reaction equation
Cl.[CH3:2][Si:3]([CH3:20])([CH3:19])[CH2:4][CH2:5][O:6][CH2:7][N:8]1[C:12]2=[N:13][CH:14]=[C:15]([NH:17][NH2:18])[N:16]=[C:11]2[CH:10]=[CH:9]1.[C:21]([O:25][C:26]([N:28]1[CH2:33][CH2:32][C@@H:31]([CH3:34])[C@H:30]([C:35](O)=[O:36])[CH2:29]1)=[O:27])([CH3:24])([CH3:23])[CH3:22]>>[C:21]([O:25][C:26]([N:28]1[CH2:33][CH2:32][C@@H:31]([CH3:34])[C@H:30]([C:35]([NH:18][NH:17][C:15]2[N:16]=[C:11]3[CH:10]=[CH:9][N:8]([CH2:7][O:6][CH2:5][CH2:4][Si:3]([CH3:20])([CH3:19])[CH3:2])[C:12]3=[N:13][CH:14]=2)=[O:36])[CH2:29]1)=[O:27])([CH3:23])([CH3:24])[CH3:22]

Participants

3

Reactant 2

HCID 66839317[5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-hydrazine hydrochlorideHCID 86317481trans-1-Tert-butoxycarbonyl-4-methyl-piperidine-3-carboxylic acid

Product 1

HCID 86650162(+/-)-3-{N'-[5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-hydrazinocarbonyl}-trans-4-methyl-piperidine-1-carboxylic acid tert-butylesterYield 24.8%

Procedure

A mixture of [5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-hydrazine hydrochloride (510 mg, 1.6 mmol, from example 15) and trans-(+/−)-4-methyl-piperidine-1,3-dicarboxylic acid 1-tert-butyl ester (480 mg, 1.9 mmol) were reacted under similar conditions to those described in example 16,to provide a crude product. Purification by preparative TLC, eluting with 55% ethyl acetate in hexanes afforded 200 mg of (+/−)-3-{N′-[5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-hydrazinocarbonyl}-trans-4-methyl-piperidine-1-carboxylic acid tert-butylester as a brown viscous oil. MS (M+H)+=505.

Workup

  1. customwere reacted under similar conditions to
  2. customprovide a crude product
  3. customPurification by preparative TLC
  4. washeluting with 55% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-516411a5d0444504a2406e4dc25b0151
Source dataset
uspto-grants-2013_01
Patent number
US08361962B2

Reaction notes

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