Trifluoroacetic acid → HCID 66785035, compound

HRID 1096602Notes

Reaction equation

HRID 1096602 reaction equation
C1C2C(COC([NH:18][CH:19]([CH:43]3[CH2:48][CH2:47][N:46](C(OC(C)(C)C)=O)[CH2:45][CH2:44]3)[CH2:20][C:21]([N:23]3[CH2:28][CH2:27][CH2:26][C@@H:25]([C:29]4[N:33]([CH2:34][CH2:35][CH2:36][O:37][CH3:38])[C:32]5[CH:39]=[CH:40][CH:41]=[CH:42][C:31]=5[N:30]=4)[CH2:24]3)=[O:22])=O)C3C(=CC=CC=3)C=2C=CC=1.FC(F)(F)C(O)=O.N1CCCCC1>C(Cl)Cl.CN(C=O)C.CC#N.O>[NH2:18][CH:19]([CH:43]1[CH2:48][CH2:47][NH:46][CH2:45][CH2:44]1)[CH2:20][C:21]([N:23]1[CH2:28][CH2:27][CH2:26][C@@H:25]([C:29]2[N:33]([CH2:34][CH2:35][CH2:36][O:37][CH3:38])[C:32]3[CH:39]=[CH:40][CH:41]=[CH:42][C:31]=3[N:30]=2)[CH2:24]1)=[O:22]

Participants

8

Reactant 3

HCID 6422Trifluoroacetic acidHCID 8082PiperidineHCID 66786466HCID 66786466, compound

Product 1

HCID 66785035HCID 66785035, compoundYield 60%

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

Compound 28A (0.293 mmol max, crude oil) was added to a 10 mL round-bottomed flask equipped for stirring under nitrogen and dissolved in CH2Cl2(2 mL). Trifluoroacetic acid (2 mL) was then added and the solution was stirred at room temperature for 2 hr. The solvent was removed in-vacuo affording a clear colored oil. This oil was re-dissolved in DMF (3 mL) and piperidine (0.500 mL) and allowed to stir at room temperature for 3 hr. This reaction solution was then directly purified by preparative LC/MS (5-50% CH3CN in H2O). The resultant fractions were collected and the solvent was removed in-vacuo affording a clear colored oil. This oil was re-dissolved in CH3CN (1 mL) and water (2 mL). The resultant solution was frozen and lyophilized to afford 3-amino-1-((R)-3-(1-(3-methoxypropyl)-1H-benzo[d]imidazol-2-yl)piperidin-1-yl)-3-(piperidin-4-yl)propan-1-one (94) as its bis-trifluoroacetic acid salt and as a clear oil (0.176 mmol, 0.118 g, 60% yield over 3-steps). ESI-MS: m/z 428.5 (M+H)+.

Workup

  1. customequipped
  2. stirringthe solution was stirred at room temperature for 2 hr
  3. customThe solvent was removed in-vacuo
  4. customaffording a clear colored oil
  5. stirringto stir at room temperature for 3 hr
  6. customThis reaction solution was then directly purified by preparative LC/MS (5-50% CH3CN in H2O)
  7. customThe resultant fractions were collected
  8. customthe solvent was removed in-vacuo
  9. customaffording a clear colored oil

Sources & evidence

ORD record
ord-c3336a2c4f164238863bbbf59ff1fce3
Source dataset
uspto-grants-2012_03
Patent number
US08138168B1

Reaction notes

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