Ammonium formate → 4-Amino-3-{6-hydroxy-1-[4-(2-pyrrolidin-1-yl-ethoxy)phenyl]-3,4-dihydro-1H-isoquinoline-2-sulfonyl}pent-3-en-2-one

HRID 397086Notes

Reaction equation

HRID 397086 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[CH:15]([C:19]1[CH:24]=[CH:23][C:22]([O:25][CH2:26][CH2:27][N:28]3[CH2:32][CH2:31][CH2:30][CH2:29]3)=[CH:21][CH:20]=1)[N:14]([S:33]([C:36]1[C:37]([CH3:42])=[N:38][O:39][C:40]=1[CH3:41])(=[O:35])=[O:34])[CH2:13][CH2:12]2)C1C=CC=CC=1.C([O-])=O.[NH4+]>CO.[OH-].[OH-].[Pd+2]>[NH2:38][C:37]([CH3:42])=[C:36]([S:33]([N:14]1[CH2:13][CH2:12][C:11]2[C:16](=[CH:17][CH:18]=[C:9]([OH:8])[CH:10]=2)[CH:15]1[C:19]1[CH:20]=[CH:21][C:22]([O:25][CH2:26][CH2:27][N:28]2[CH2:32][CH2:31][CH2:30][CH2:29]2)=[CH:23][CH:24]=1)(=[O:35])=[O:34])[C:40](=[O:39])[CH3:41]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 18172419HCID 18172419, compound

Product 1

HCID 698785634-Amino-3-{6-hydroxy-1-[4-(2-pyrrolidin-1-yl-ethoxy)phenyl]-3,4-dihydro-1H-isoquinoline-2-sulfonyl}pent-3-en-2-oneYield 76%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

A mixture of 6-benzyloxy-2-(3,5-dimethylisoxazole-4-sulfonyl)-1-[4-(2-pyrrolidin-1-yl-ethoxy)phenyl]-1,2,3,4-tetrahydroisoquinoline (0.036 g, 0.061 mmol), ammonium formate (0.077 g, 1.22 mmol), and 20% Pd(OH)2/C (0.020 g) in MeOH (20 ml) was refluxed under N2 for 1.5 hr, then filtered through Celite. The filtrate was evaporated in vacuo to a yellow residue that was suspended in a mixture of H2O(3 ml) and sat. NaHCO3 solution (3 ml), then extracted with CH2Cl2 (3×3 ml). The combined organic extracts were dried over MgSO4 and concentrated in vacuo to give 0.023 g (76% yield) of yellow oil. Further purification by preparative TLC, eluting with SiO2, EtOAc:MeOH (1:1), gave 0.019 g (63% yield) of colorless oil.

Workup

  1. temperaturewas refluxed under N2 for 1.5 hr
  2. filtrationfiltered through Celite
  3. customThe filtrate was evaporated in vacuo to a yellow residue that
  4. additionwas suspended in a mixture of H2O(3 ml) and sat. NaHCO3 solution (3 ml)
  5. extractionextracted with CH2Cl2 (3×3 ml)
  6. dry with materialThe combined organic extracts were dried over MgSO4
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7079f68684fa42e5a7da2e54bae76d46
Source dataset
uspto-grants-2003_08
Patent number
US06608203B2

Reaction notes

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