HCID 67568320, compound → HCID 67569415, compound

HRID 1418400Notes

Reaction equation

HRID 1418400 reaction equation
[ClH:1].[N+:2]([C:5]1[CH:28]=[CH:27][C:8]([C:9]([N:11]2[CH2:26][CH2:25][C:14]3([N:23]=[C:22]([NH2:24])[C:21]4[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=4)[NH:15]3)[CH2:13][CH2:12]2)=[O:10])=[CH:7][CH:6]=1)([O-])=O.[H][H]>[Pd].C(O)C>[ClH:1].[ClH:1].[NH2:2][C:5]1[CH:6]=[CH:7][C:8]([C:9]([N:11]2[CH2:26][CH2:25][C:14]3([N:23]=[C:22]([NH2:24])[C:21]4[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=4)[NH:15]3)[CH2:13][CH2:12]2)=[O:10])=[CH:27][CH:28]=1

Participants

5

Reactant 2

HCID 67568320HCID 67568320, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 67569415HCID 67569415, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A suspension of 1-(4-Nitrobenzoyl)spiro[piperidine-4,2'(1'H)-quinazoline]4'-amine hydrochloride (Example 57)(181 mg, 0.45 mnmol) and 10% palladium on charcoal (18 mg, 10 mol%) in ethanol (20 ml) was stirred under 3 atrmospheres pressure of hydrogen for 20 h. The mixture was filtered and concentrated in vacuo. Purification by RP-HPLC eluting is with trifluoroacetic acid/water/methanol (1:90:10, increasing the gradient to 1:5:95) gave a yellow foam, MS (+FAB) 336 ([M+H]+), 1H NMR (d6 -DMSO) 10.64 (1H, s), 9.30 (1H, s), 8.75 (1H, s), 7.86 (1H, d, J 8.0 Hz), 7.78 (1H, s), 7.48 (1H, t, J 7.7 Hz), 7.42 (2H, d, J 8.2 Hz), 7.23 (2H, d, J 8.1 Hz), 6.94 (1H, d, J 8.3 Hz), 6.81 (1H, t, J 7.6 Hz), 4.05 (2H, br. s), 3.75 (2H, br. s), 3.63 (2H, br. s), 1.97 (2H, br. s), 1.84 (2H, br. s).

Workup

  1. customfor 20 h
  2. filtrationThe mixture was filtered
  3. concentrationconcentrated in vacuo
  4. customPurification by RP-HPLC
  5. washeluting
  6. temperatureincreasing the gradient to 1:5:95)
  7. customgave a yellow foam, MS (+FAB) 336 ([M+H]+), 1H NMR (d6 -DMSO) 10.64 (1H, s), 9.30 (1H, s), 8.75 (1H, s), 7.86 (1H, d, J 8.0 Hz), 7.78 (1H, s), 7.48 (1H, t, J 7.7 Hz), 7.42 (2H, d, J 8.2 Hz), 7.23 (2H, d, J 8.1 Hz), 6.94 (1H, d, J 8.3 Hz), 6.81 (1H, t, J 7.6 Hz), 4.05 (2H, br. s), 3.75 (2H, br. s), 3.63 (2H, br. s), 1.97 (2H, br. s), 1.84 (2H, br. s)

Sources & evidence

ORD record
ord-5f17a74745b34209bbf359f565c1a7ef
Source dataset
uspto-grants-1999_03
Patent number
US05883102

Reaction notes

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