HCID 71253068, compound → HCID 54589064, compound

HRID 571113Notes

Reaction equation

HRID 571113 reaction equation
[C:1]([C:5]1[CH:9]=[C:8]([NH:10][C:11](=[O:36])[NH:12][C:13]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[C:16]([O:23][C:24]3[CH:29]=[CH:28][N:27]=[C:26]([NH:30][C:31](=[O:35])[CH2:32][O:33][CH3:34])[CH:25]=3)=[CH:15][CH:14]=2)[N:7]([C:37]2[CH:42]=[CH:41][C:40]([N+:43]([O-])=O)=[CH:39][CH:38]=2)[N:6]=1)([CH3:4])([CH3:3])[CH3:2].[H][H]>CO.CC(O)=O.[Pt]>[NH2:43][C:40]1[CH:39]=[CH:38][C:37]([N:7]2[C:8]([NH:10][C:11](=[O:36])[NH:12][C:13]3[C:22]4[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=4)[C:16]([O:23][C:24]4[CH:29]=[CH:28][N:27]=[C:26]([NH:30][C:31](=[O:35])[CH2:32][O:33][CH3:34])[CH:25]=4)=[CH:15][CH:14]=3)=[CH:9][C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])=[N:6]2)=[CH:42][CH:41]=1

Participants

6

Reactant 2

HCID 71253068HCID 71253068, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 54589064HCID 54589064, compound

Reagents, catalysts & solvents 3

HCID 23939PlatinumCatalystHCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

A solution of N-(4-(4-(3-(3-tert-butyl-1-(4-nitrophenyl)-1H-pyrazol-5-yl)ureido)naphthalen-1-yloxy)pyridin-2-yl)-2-methoxyacetamide (270 mg, 0.443 mmol) in a mixture of MeOH (20 mL) and AcOH (1.0 mL) was subjected to hydrogenation by passage through a Thales H-cube (1.0 mL min−1, 40° C., 55 mm, 10% Pt—C Cat-Cart, full hydrogen mode). The reaction mixture was evaporated in vacuo and the residue was partitioned between EtOAc (15 mL) and saturated aq. NaHCO3 (15 mL). The organic layer was separated and was washed with brine (15 mL) and then dried and evaporated in vacuo. The residue was purified by flash column chromatography (SiO2, EtOAc in isohexane, 20-100%, gradient elution) to afford the title compound, Example 1, as a pale brown solid (115 mg, 43%); Rt 4.87 min (Method 1 basic); m/z 580 (M+H)+ (ES+); 1H NMR (400 MHz, DMSO-d6) δ: 1.25 (9H, s), 3.30 (3H, s), 3.98 (2H, s), 5.41 (2H, s), 6.34 (1H, s), 6.68-6.71 (3H, overlapping m), 7.14 (2H, d), 7.33 (1H, d), 7.57 (1H, m), 7.63-7.67 (2H, overlapping m), 7.83 (1H, d), 7.98 (1H, dd), 8.09 (1H, d), 8.18 (1H, d), 8.65 (1H, s), 9.18 (1H, s), 10.04 (1H, s).

Workup

  1. customThe reaction mixture was evaporated in vacuo
  2. customthe residue was partitioned between EtOAc (15 mL) and saturated aq. NaHCO3 (15 mL)
  3. customThe organic layer was separated
  4. washwas washed with brine (15 mL)
  5. customdried
  6. customevaporated in vacuo
  7. customThe residue was purified by flash column chromatography (SiO2, EtOAc in isohexane, 20-100%, gradient elution)

Sources & evidence

ORD record
ord-8e5d63005570419c9fc3c3d9967f052f
Source dataset
uspto-grants-2015_05
Patent number
US09024041B2

Reaction notes

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