Trifluoroacetic acid → 3-[1-(3-Amino-propyl)-piperidin-4-yl]-7-[2-(3-fluoro-phenyl)-ethyl]-3H,9H-10-oxa-1,3,9-triaza-anthracen-2-one

HRID 570158Notes

Reaction equation

HRID 570158 reaction equation
C(OC(=O)[NH:7][CH2:8][CH2:9][CH2:10][N:11]1[CH2:16][CH2:15][CH:14]([N:17]2[CH:30]=[C:29]3[C:20]([NH:21][C:22]4[C:27]([O:28]3)=[CH:26][CH:25]=[C:24]([CH2:31][CH2:32][C:33]3[CH:38]=[CH:37][CH:36]=[C:35]([F:39])[CH:34]=3)[CH:23]=4)=[N:19][C:18]2=[O:40])[CH2:13][CH2:12]1)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[NH2:7][CH2:8][CH2:9][CH2:10][N:11]1[CH2:16][CH2:15][CH:14]([N:17]2[CH:30]=[C:29]3[C:20]([NH:21][C:22]4[C:27]([O:28]3)=[CH:26][CH:25]=[C:24]([CH2:31][CH2:32][C:33]3[CH:38]=[CH:37][CH:36]=[C:35]([F:39])[CH:34]=3)[CH:23]=4)=[N:19][C:18]2=[O:40])[CH2:13][CH2:12]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66578486[3-(4-{7-[2-(3-Fluoro-phenyl)-ethyl]-2-oxo-2,9-dihydro-10-oxa-1,3,9-triaza-anthracen-3-yl}-piperidin-1-yl)-propyl]-carbamic acid tert-butyl ester

Product 1

HCID 510499793-[1-(3-Amino-propyl)-piperidin-4-yl]-7-[2-(3-fluoro-phenyl)-ethyl]-3H,9H-10-oxa-1,3,9-triaza-anthracen-2-oneYield 99%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of [3-(4-{7-[2-(3-fluoro-phenyl)-ethyl]-2-oxo-2,9-dihydro-10-oxa-1,3,9-triaza-anthracen-3-yl}-piperidin-1-yl)-propyl]-carbamic acid tert-butyl ester (94 mg, 0.167 mmol, 1 equiv) in dichloromethane (10 mL) at 23° C. was added trifluoroacetic acid (4.0 mL). The reaction was stirred for 30 min then concentrated. The residue was dissolved in water (10 mL) then treated with 1.0 N aqueous hydrochloric acid (2.0 mL). The resulting solution was concentrated, and then the residue was re-dissolved in water (10 mL), treated with hydrochloric acid (2.0 mL) and concentrated. The residue was dissolved in water (10 mL) and then the resulting solution was frozen and then lyophilized to give 88 mg (0.165 mmol, 99%) of the desired product (dihydrochloride salt) as a yellow solid. LCMS (EI): 464.1 (M+H)+.

Workup

  1. concentrationthen concentrated
  2. dissolutionThe residue was dissolved in water (10 mL)
  3. additionthen treated with 1.0 N aqueous hydrochloric acid (2.0 mL)
  4. concentrationThe resulting solution was concentrated
  5. dissolutionthe residue was re-dissolved in water (10 mL)
  6. additiontreated with hydrochloric acid (2.0 mL)
  7. concentrationconcentrated
  8. dissolutionThe residue was dissolved in water (10 mL)
  9. temperaturethe resulting solution was frozen

Sources & evidence

ORD record
ord-a9f06028c5bf496aa76f5da51973145c
Source dataset
uspto-grants-2015_05
Patent number
US09023843B2

Reaction notes

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