Hydrochloric Acid → HCID 25032630, compound

HRID 657069Notes

Reaction equation

HRID 657069 reaction equation
[NH2:1][CH2:2][C@@H:3]1[CH2:8][CH2:7][CH2:6][N:5]([CH2:9][CH2:10][N:11]2[C:20]3[C:15](=[CH:16][CH:17]=[C:18]([F:21])[CH:19]=3)[CH:14]=[CH:13][C:12]2=[O:22])[CH2:4]1.[Cl:23][C:24]1[C:33]([CH:34]=O)=[N:32][C:31]2[NH:30][C:29](=[O:36])[CH2:28][O:27][C:26]=2[CH:25]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].Cl.C1(N)C(F)=C(F)C(F)=C(N)C=1F.Cl.Cl>CO.CCOCC.C(Cl)Cl>[Cl:23][C:24]1[C:33]([CH2:34][NH:1][CH2:2][C@@H:3]2[CH2:8][CH2:7][CH2:6][N:5]([CH2:9][CH2:10][N:11]3[C:20]4[C:15](=[CH:16][CH:17]=[C:18]([F:21])[CH:19]=4)[CH:14]=[CH:13][C:12]3=[O:22])[CH2:4]2)=[N:32][C:31]2[NH:30][C:29](=[O:36])[CH2:28][O:27][C:26]=2[CH:25]=1

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 149026Tetrafluoro-m-phenylenediamine dihydrochlorideHCID 5049666Sodium triacetoxyborohydrideHCID 574868727-Chloro-3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazine-6-carbaldehydeHCID 68991212HCID 68991212, compound

Product 1

HCID 25032630HCID 25032630, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 1-{2-[(3S)-3-(aminomethyl)-1-piperidinyl]ethyl}-7-fluoro-2(1H)-quinolinone (90 mg; 0.3 mmol) and 7-chloro-3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazine-6-carboxaldehyde (for a synthesis see WO2003064421, Example 15(c)) (64 mg, 0.3 mmol) in methanol (2 ml), DCM (4 ml) was stirred at rt overnight. Sodium triacetoxyborohydride (0.127 g; 0.6 mmol) was added and the mixture was stirred at room temperature for 1 h. The reaction was evaporated and chromatographed on silica gel, eluting with 0-15% methanol-DCM-1% NH4OH to give an oil. The oil was treated with 1M HCl in Et2O to give the title compound (14 mg) as the dihydrochloride salt. 1H NMR (400 MHz, CD3OD) δ ppm 1.07 (s, 1H) 1.59-1.69 (m, 1H) 1.71-1.83 (m, 2H) 1.83-1.94 (m, 2H) 2.15-2.23 (m, 1H) 2.56-2.61 (m, 21H) 2.63-2.75 (m, 3H) 2.97 (s, 1H) 3.13-3.20 (m, 1H) 3.90 (s, 2H) 4.49 (td, J=14.21, 7.71 Hz, 2H) 6.67 (d, J=9.60 Hz, 1H) 7.11 (td, J=8.46, 2.27 Hz, 1H) 7.38-7.50 (m, 2H) 7.75 (dd, J=8.72, 6.19 Hz, 1H) 7.91 (d, J=9.60 Hz, 1H)

Workup

  1. customThe reaction was evaporated
  2. customchromatographed on silica gel
  3. washeluting with 0-15% methanol-DCM-1% NH4OH
  4. customto give an oil

Sources & evidence

ORD record
ord-85ece8654bb4437187b1c3dd23b60796
Source dataset
uspto-grants-2011_12
Patent number
US08071592B2

Reaction notes

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