Sodium Iodide → HCID 11948442, compound

HRID 885692Notes

Reaction equation

HRID 885692 reaction equation
[CH3:1][O:2][C:3]1[N:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[CH:8][CH:7]=[C:6]2[N:13]1[CH:21]=[C:20]2[C:15]([CH2:16][CH2:17][CH:18]([NH2:22])[CH2:19]2)=[N:14]1.C([O-])([O-])=O.[K+].[K+].Cl[CH2:30][C:31]([NH:33][C:34]1[CH:39]=[C:38]([F:40])[CH:37]=[C:36]([F:41])[CH:35]=1)=[O:32].[Na+].[I-]>CN(C=O)C.CCOC(C)=O>[F:40][C:38]1[CH:39]=[C:34]([NH:33][C:31](=[O:32])[CH2:30][NH:22][CH:18]2[CH2:17][CH2:16][C:15]3[C:20](=[CH:21][N:13]([C:6]4[C:5]5[C:10](=[CH:11][CH:12]=[C:3]([O:2][CH3:1])[N:4]=5)[N:9]=[CH:8][CH:7]=4)[N:14]=3)[CH2:19]2)[CH:35]=[C:36]([F:41])[CH:37]=1

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 16227189874804-29-2HCID 595606482-(6-Methoxy-[1,5]naphthyridin-4-yl)4,5,6,7-tetrahydro-2H-indazol-5-ylamine

Product 1

HCID 11948442HCID 11948442, compoundYield 64.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 2-(6-methoxy-[1,5]naphthyridin-4-yl)-4,5,6,7-tetrahydro-2H-indazol-5-ylamine (30 mg, 0.1 mmol) in DMF (1 mL) were added K2CO3 (40 mg, 0.3 mmol) and 2-chloro-N-(3,5-difluoro-phenyl)-acetamide (20 mg, 0.1 mmol), and the mixture was stirred for 15 h. A catalytic amount of NaI was added and the mixture heated at 50° C. for 15 h. The mixture was diluted with EtOAc (25 mL), washed with brine (4×10 mL), dried (MgSO4) and concentrated. The resulting residue was purified on SiO2 (0-5% CH3OH/CH2Cl2) to provide 30 mg (64%) of the title compound as a pale yellow solid. MS (ESI): exact mass calculated for C24H22F2N6O2, 464.18; m/z found, 465.3 [M+H]+. 1H NMR (500 MHz, CDCl3): 9.30 (br s, 1H), 9.08 (s, 1H), 8.76 (d, J=9.2, 1H), 8.24 (d, J=5.9, 1H), 8.19 (d, J=5.1, 1H), 7.15 (d, J=9.1, 1H), 6.93-6.87 (m, 2H), 6.26 (tt, J=8.9, 2.3, 1H), 3.89 (s, 3H), 3.59 (d, J=17.7, 1H), 3.36 (d, J=17.7, 1H), 3.26-3.23 (m, 1H), 3.08-3.02 (m, 1H), 2.93-2.85 (m, 2H), 2.62 (dd, J=15.7, 5.7, 1H), 2.12-2.08 (m, 1H), 2.00-1.96 (m, 1H).

Workup

  1. washwashed with brine (4×10 mL)
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated
  4. customThe resulting residue was purified on SiO2 (0-5% CH3OH/CH2Cl2)

Sources & evidence

ORD record
ord-7b0958712dd74216846f0a29d35d9814
Source dataset
uspto-grants-2012_08
Patent number
US08242275B2

Reaction notes

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