Potassium Iodide → HCID 58529666, compound

HRID 1972843Notes

Reaction equation

HRID 1972843 reaction equation
[CH2:1]([N:8]1[CH:16]=[C:15]2[C:10]([CH:11]=[C:12]([C:17]3[CH:18]=[C:19]([CH:27]4[CH2:31][CH2:30][NH:29][CH2:28]4)[N:20]4[C:25]=3[C:24]([NH2:26])=[N:23][CH:22]=[N:21]4)[CH:13]=[CH:14]2)=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[CH2:33][CH2:34][O:35][CH3:36].[I-].[K+]>CN(C=O)C.C(N(CC)CC)C>[CH2:1]([N:8]1[CH:16]=[C:15]2[C:10]([CH:11]=[C:12]([C:17]3[CH:18]=[C:19]([CH:27]4[CH2:31][CH2:30][N:29]([CH2:33][CH2:34][O:35][CH3:36])[CH2:28]4)[N:20]4[C:25]=3[C:24]([NH2:26])=[N:23][CH:22]=[N:21]4)[CH:13]=[CH:14]2)=[N:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 4875Potassium IodideHCID 809722-Bromoethyl methyl etherHCID 58529326HCID 58529326, compound

Product 1

HCID 58529666HCID 58529666, compoundYield 19.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 5-(2-benzyl-2H-indazol-6-yl)-7-pyrrolidin-3-ylpyrrolo[2,1-f][1,2,4]triazin-4-amine (50 mg, 0.122 mmol) in 2 mL of DMF, triethylamine is added (34 uL, 0.244 mmol) followed by 1-bromo-2-methoxyethane (36 uL, 0.256 mmol). A spatula tip of potassium iodide was added and the reaction heated at 60° C. for 48 hours. The reaction was cooled and then partitioned between EtOAc (50 mL) and water (25 mL). The organic layer was washed with water (5×15 mL) to remove DMF. The EtOAc layer was the dried with Na2SO4 and then concentrated to yield an off-white solid. The solid was recrystallized from EtOAc-hexanes to yield 11 mg (19%) of title compound. 1H NMR (300 MHz, DMSO-d6) δ 8.53 (s, 1 H), 7.88 (s, 1 H), 7.80 (d 1 H), 7.58 (s, 1 H), 7.35 (m, 5 H), 7.15 (d, 1 H), 6.66 (s, 1 H), 5.64 (s, 2 H), 3.80 (m, 2H), 3.45 (t, 2H), 3.30-3.05 (m, 6 H), 2.70-2.50 (m, 2 H), 2.25 (m, 1 H), 1.97 (m, 1H); ES-MS m/z 468.2 [M+H]+, HPLC RT (min) 2.17.

Workup

  1. temperatureThe reaction was cooled
  2. custompartitioned between EtOAc (50 mL) and water (25 mL)
  3. washThe organic layer was washed with water (5×15 mL)
  4. customto remove DMF
  5. dry with materialdried with Na2SO4
  6. concentrationconcentrated
  7. customto yield an off-white solid
  8. customThe solid was recrystallized from EtOAc-hexanes

Sources & evidence

ORD record
ord-8510105c255c4aa4a9cd2f3f19d44688
Source dataset
uspto-grants-2013_04
Patent number
US08431695B2

Reaction notes

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