Hydrochloric Acid → HCID 68571229, compound

HRID 2378962Notes

Reaction equation

HRID 2378962 reaction equation
[O:1]=[C:2]1[NH:8][C:7]2[N:9]=[CH:10][CH:11]=[CH:12][C:6]=2[CH2:5][CH2:4][N:3]1[CH:13]1[CH2:18][CH2:17][N:16](C(OC(C)(C)C)=O)[CH2:15][CH2:14]1.FC(F)(F)C(O)=O.[ClH:33].C(OCC)C>ClCCl>[ClH:33].[ClH:33].[NH:16]1[CH2:15][CH2:14][CH:13]([N:3]2[CH2:4][CH2:5][C:6]3[CH:12]=[CH:11][CH:10]=[N:9][C:7]=3[NH:8][C:2]2=[O:1])[CH2:18][CH2:17]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 6422Trifluoroacetic acidHCID 59006377HCID 59006377, compound

Product 1

HCID 68571229HCID 68571229, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl 4-(2-oxo-4,5-dihydro-1H-pyrido[2,3-d][1,3]diazepin-3(2H)-yl)piperidine-1-carboxylate (0.51 g, 1.472 mmol) was dissolved in dichloromethane (8 ml). Trifluoroacetic acid (2 ml, 26.0 mmol) was added to the solution. The mixture was stirred at room temperature for 4 hours. All volatiles were removed by roto-vap. Residue was dissolved in dichloromethane (10 mL). 2M Hydrogen chloride in diethyl ether (2.58 ml, 5.15 mmol) was added to the mixture. The mixture was stirred at room temperature for 15 minutes and then all volatiles were removed. The resulting off-white solid was washed with anhydrous diethyl ether four times to afford the title compound as white solid in 99% yield. 1H NMR (500 MHz, D2O) δ ppm 8.01-8.29 (m, 2 H) 7.38 (t, J=6.71 Hz, 1 H) 4.63-4.88 (m, 2 H) 4.29-4.53 (m, 1 H) 3.61-3.71 (m, 2 H) 3.45-3.62 (m, 2 H) 3.01-3.27 (m, 4 H) 1.93-2.21 (m, 4 H).

Workup

  1. customAll volatiles were removed by roto-vap
  2. dissolutionResidue was dissolved in dichloromethane (10 mL)
  3. stirringThe mixture was stirred at room temperature for 15 minutes
  4. customall volatiles were removed
  5. washThe resulting off-white solid was washed with anhydrous diethyl ether four times

Sources & evidence

ORD record
ord-f1de1e59c41147a2bbb6c00af9411ad9
Source dataset
uspto-grants-2008_12
Patent number
US07470680B2

Reaction notes

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