5-(4-tert-butoxycarbonylamino-pyridin-3-yl)-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester → 3-(1,2,3,4-Tetrahydro-isoquinolin-5-yl)-pyridin-4-ylamine

HRID 2183720Notes

Reaction equation

HRID 2183720 reaction equation
C(OC([N:8]1[CH2:17][CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][C:14]=2[C:18]2[CH:19]=[N:20][CH:21]=[CH:22][C:23]=2[NH:24]C(OC(C)(C)C)=O)[CH2:9]1)=O)(C)(C)C>FC(F)(F)C(O)=O.ClCCl>[CH2:9]1[C:10]2[C:15](=[C:14]([C:18]3[CH:19]=[N:20][CH:21]=[CH:22][C:23]=3[NH2:24])[CH:13]=[CH:12][CH:11]=2)[CH2:16][CH2:17][NH:8]1

Participants

4

Reactant 1

HCID 695955295-(4-tert-butoxycarbonylamino-pyridin-3-yl)-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester

Product 1

HCID 219836983-(1,2,3,4-Tetrahydro-isoquinolin-5-yl)-pyridin-4-ylamineYield 79.3%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

5-(4-tert-Butoxycarbonylamino-pyridin-3-yl)-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester (0.18 g, 0.42 mmol) was dissolved at room temperature in 20 mL of 10% trifluoroacetic acid in dichloromethane and stirred to room temperature for 18 h. The volatiles were evaporated, the residue was suspended in toluene and evaporated again. The residue was purified by flash chromatography eluting with 7% methanol in dichloromethane containing 0.7% of ammonium hydroxide to yield 0.075 g of 3-(1,2,3,4-tetrahydro-isoquinolin-5-yl)-pyridin-4-ylamine.

Workup

  1. customThe volatiles were evaporated
  2. customevaporated again
  3. customThe residue was purified by flash chromatography
  4. washeluting with 7% methanol in dichloromethane containing 0.7% of ammonium hydroxide

Sources & evidence

ORD record
ord-dd43f54af1034fdea7c4379a22c26a66
Source dataset
uspto-grants-2005_05
Patent number
US06900220B2

Reaction notes

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