4-[1-(2,5-Dichlorobenzyl)-1,2,3,4-tetrahydropyrido[2,3-b]pyrazin-7-yl]-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester → 1-(2,5-Dichlorobenzyl)-7-(1,2,3,6-tetrahydropyridin-4-yl)-1,2,3,4-tetrahydropyrido[2,3-b]pyrazine

HRID 659400Notes

Reaction equation

HRID 659400 reaction equation
C(OC([N:8]1[CH2:13][CH:12]=[C:11]([C:14]2[CH:32]=[N:31][C:17]3[NH:18][CH2:19][CH2:20][N:21]([CH2:22][C:23]4[CH:28]=[C:27]([Cl:29])[CH:26]=[CH:25][C:24]=4[Cl:30])[C:16]=3[CH:15]=2)[CH2:10][CH2:9]1)=O)(C)(C)C>C(Cl)Cl.FC(F)(F)C(O)=O>[Cl:30][C:24]1[CH:25]=[CH:26][C:27]([Cl:29])=[CH:28][C:23]=1[CH2:22][N:21]1[CH2:20][CH2:19][NH:18][C:17]2[N:31]=[CH:32][C:14]([C:11]3[CH2:12][CH2:13][NH:8][CH2:9][CH:10]=3)=[CH:15][C:16]1=2

Participants

3

Reactant 1

HCID 578858414-[1-(2,5-Dichlorobenzyl)-1,2,3,4-tetrahydropyrido[2,3-b]pyrazin-7-yl]-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester

Product 1

HCID 578860261-(2,5-Dichlorobenzyl)-7-(1,2,3,6-tetrahydropyridin-4-yl)-1,2,3,4-tetrahydropyrido[2,3-b]pyrazineYield 84%

Reagents, catalysts & solvents 1

HCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

4-[1-(2,5-Dichlorobenzyl)-1,2,3,4-tetrahydropyrido[2,3-b]pyrazin-7-yl]-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester (105 mg) was dissolved in CH2Cl2/trifluoroacetic acid (3:1, v/v) and stirred at room temperature for two (2) hours. The reaction mixture was concentrated, diluted with CH2Cl2, washed with NaHCO3 (×2), dried, filtered, and concentrated to give the title compound as a pale orange solid (84% yield). M.p. 133-136° C., LCMS: m/z=375.13 (M+H+), 1H-NMR (DMSO-d6, 400 MHz) δ 2.30-2.38 (m, 2H), 3.00-3.06 (m, 1H), 3.28-3.34 (m, 2H), 3.52-3.58 (m, 2H), 4.49 (s, 2H), 5.80 (s, 1H), 6.47 (s, 1H), 6.59 (s, 1H), 7.29 (d, J=2.5 Hz, 1H), 7.37-7.42 (m, 2H), 7.54 (d, J=8.6 Hz, 1H).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additiondiluted with CH2Cl2
  3. washwashed with NaHCO3 (×2)
  4. customdried
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-366a197260e14457aca3cc6028c66540
Source dataset
uspto-grants-2011_12
Patent number
US08080561B2

Reaction notes

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