Hydrochloric Acid → HCID 58877841, compound

HRID 1664200Notes

Reaction equation

HRID 1664200 reaction equation
[CH2:1]([O:8][C:9]1[C:24](=[O:25])[N:13]2[CH2:14][CH2:15][O:16][CH2:17][C:18]3([CH2:23][CH2:22][O:21][CH2:20][CH2:19]3)[C:12]2=[N:11][C:10]=1[C:26](O)=[O:27])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:29][CH2:30][C:31]1[CH:36]=[CH:35][C:34]([F:37])=[CH:33][C:32]=1[N:38]1[C:42](=[O:43])[N:41]([CH3:44])[CH:40]=[N:39]1.C(N(C(C)C)CC)(C)C.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.Cl>CC#N>[CH2:1]([O:8][C:9]1[C:24](=[O:25])[N:13]2[CH2:14][CH2:15][O:16][CH2:17][C:18]3([CH2:19][CH2:20][O:21][CH2:22][CH2:23]3)[C:12]2=[N:11][C:10]=1[C:26]([NH:29][CH2:30][C:31]1[CH:36]=[CH:35][C:34]([F:37])=[CH:33][C:32]=1[N:38]1[C:42](=[O:43])[N:41]([CH3:44])[CH:40]=[N:39]1)=[O:27])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 81531DiisopropylethylamineHCID 4641409(Dimethylamino)-N,N-dimethyl(3H-(1,2,3)triazolo(4,5-b)pyridin-3-yloxy)methaniminiumHCID 58877861HCID 58877861, compoundHCID 58877863HCID 58877863, compound

Product 1

HCID 58877841HCID 58877841, compoundYield 89.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
23 °C

Procedure

To a solution of 3′-(benzyloxy)-4′-oxo-2,3,4′,5,6,6′,7′,9′-octahydrospiro[pyran-4,10′-pyrimido[1,2-d][1,4]oxazepine]-2′-carboxylic acid (0.095 g, 0.246 mmol) in CH3CN (15 mL) was added 1-(2-(aminomethyl)-5-fluorophenyl)-4-methyl-1H-1,2,4-triazol-5(4H)-one (0.070 g, 0.271 mmol), diisopropylethylamine (0.171 mL, 0.984 mmol) and O-(7-azabenzotriazole-1yl)-N,N,N′,N′-tetramethyluronium (0.103 g, 0.271 mmol). The reaction mixture was stirred at 23° C. for 18 hours. HCl (1N, 50 mL) was added and the organic material was extracted with EtOAc (3×50 mL). The combined organic phases were washed with H2O (50 mL), brine (50 mL), dried over MgSO4 and concentrated in vacuo. The crude material was purified on Silica gel column (Biotage™), eluted with EtOAc:Hex (1:1) to EtOAc 100% to afford the title compound as a white solid (0.130 g, 77%): 1H NMR (400 MHz, CDCl3) δ 8.54 (1 H, brs), 7.67 (1H, dd, J=8.7, 6.2 Hz), 7.52 (2H, m), 7.45 (1H, s), 7.27-7.36 (3H, m), 7.22 (1H, dd, J=9.3, 2.5 Hz), 7.08 (1H, td, J=8.2, 2.5 Hz), 5.31 (2H, s), 4.54 (2 H, d, J=6.3 Hz), 4.1-3.6 (10H, m), 3.36 (3H, s), 2.4-2.2 (1H, brm), 2.1-1.6 (2H, brs). LCMS (+ESI, M+H+) m/z 591.

Workup

  1. extractionthe organic material was extracted with EtOAc (3×50 mL)
  2. washThe combined organic phases were washed with H2O (50 mL), brine (50 mL)
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe crude material was purified on Silica gel column (Biotage™)
  6. washeluted with EtOAc

Sources & evidence

ORD record
ord-5bcf01f3a4874592901a976c16a766ae
Source dataset
uspto-grants-2011_10
Patent number
US08039458B2

Reaction notes

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