Trifluoroacetic acid → HCID 14626192, compound

HRID 1638707Notes

Reaction equation

HRID 1638707 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]2[N:18]=[C:19]([CH3:34])[C:20]3[C:25]([C:26]=2[N+:27]([O-:29])=[O:28])=[CH:24][C:23]([O:30][CH3:31])=[C:22]([O:32][CH3:33])[CH:21]=3)=[O:15])[CH2:10][CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O>[OH-].[Na+]>[CH3:31][O:30][C:23]1[CH:24]=[C:25]2[C:20](=[CH:21][C:22]=1[O:32][CH3:33])[C:19]([CH3:34])=[N:18][C:17]([O:16][C:14]([N:11]1[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]1)=[O:15])=[C:26]2[N+:27]([O-:29])=[O:28]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 14626190HCID 14626190, compound

Product 1

HCID 14626192HCID 14626192, compoundYield 94.4%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

3-(4-t-Butoxycarbonylpiperazin-1-yl)carbonyloxy-6,7-dimethoxy-1-methyl-4-nitroisoquinoline (20 g, 4.20 mmol) was added in small portions over 20 minutes to trifluoroacetic acid (15 mL), stirred and cooled to -10° C. (ice-methanol bath). The mixture was stirred at -10° C. for an additional 30 minutes and was then diluted with ice-water (100 mL). The solution was basified by adding 2N NaOH (150 mL) and then extracted with methylene chloride (3×100 mL). The combined organic extracts were dried (Na2SO4), filtered and evaporated to dryness in vacuo to yield a yellow solid residue. The solid was triturated thoroughly with ether, and was the collected and dried to yield the title compound as a yellow solid (1.49 g, 94.4%), mp |300° C. (d). IR (KBr): 3356, 1731, 1620, 1569, 1515, 1213 cm-1 ; NMR (CDCl3): δ 1.67 (br, s, 1H, NH); 2.90 (s, 3H, 1-CH3), superimposed over 2.97 [br m, HN[(CH2)]2, 3.58 [br, s CON[(CH2)]2, 4.02 (s, 6H, 2×OCH3), 7.25 (s, 1H, 5- or 8-H), 7.30 (s, 1H, 5- or 8-H); MS (DCI): 377 (MH)+.

Workup

  1. stirringThe mixture was stirred at -10° C. for an additional 30 minutes
  2. extractionextracted with methylene chloride (3×100 mL)
  3. dry with materialThe combined organic extracts were dried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated to dryness in vacuo
  6. customto yield a yellow solid residue
  7. customThe solid was triturated thoroughly with ether
  8. customcollected
  9. customdried

Sources & evidence

ORD record
ord-2e8605ced6b24d608d9e96610951be50
Source dataset
uspto-grants-1989_11
Patent number
US04880817

Reaction notes

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