Triethylamine → HCID 58529391, compound

HRID 1972789Notes

Reaction equation

HRID 1972789 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]([CH2:27][CH2:28][CH2:29][CH2:30]Br)[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.[NH:32]1[CH2:36][CH2:35][CH2:34][CH2:33]1.C(N(CC)CC)C>CN(C=O)C.[I-].[Na+]>[CH2:1]([N:8]1[CH:16]=[C:15]2[C:10]([CH:11]=[C:12]([C:17]3[CH:18]=[C:19]([CH2:27][CH2:28][CH2:29][CH2:30][N:32]4[CH2:36][CH2:35][CH2:34][CH2:33]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

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 31268PyrrolidineHCID 58529675HCID 58529675, compound

Product 1

HCID 58529391HCID 58529391, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 5238Sodium IodideCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
55 °C

Procedure

To a solution of 5-(2-benzyl-2H-indazol-6-yl)-7-(4-bromobutyl)pyrrolo[2,1-f][1,2,4]triazin-4-amine (440 mg, 0.93 mmol) in DMF (5.0 mL) was added pyrrolidine (155 μL, 1.86 mmol), triethylamine (387 μl, 2.78 mmol), and sodium iodide (1.4 mg, 0.009 mmol). The reaction was heated (55° C.) for 17 h and then cooled to rt. The mixture was partitioned between ethyl acetate (25 mL) and water (25 mL). The layers were separated and the organic was washed with water (2×20 mL), brine, dried (Na2SO4) and evaporated to afford 360 mg (84%) of the desired product. 1H NMR (300 MHz, DMSO-d6) δ 8.53 (s, 1 H), 7.87 (s, 1 H), 7.78 (d, 1 H), 7.56 (s, 1 H), 7.36-7.26 (m, 5 H), 7.13 (dd, 1 H), 6.57 (s, 1 H), 5.64 (s, 2 H), 2.88 (t, 2 H), 2.42-2.33 (m, 6 H), 1.78-1.66 (m, 2 H), 1.67-1.60 (m, 4 H), 1.57-1.46 (m, 2H); ES-MS m/z 466.3 [M+H]+, HPLC RT (min) 2.20.

Workup

  1. temperaturecooled to rt
  2. customThe mixture was partitioned between ethyl acetate (25 mL) and water (25 mL)
  3. customThe layers were separated
  4. washthe organic was washed with water (2×20 mL), brine
  5. dry with materialdried (Na2SO4)
  6. customevaporated

Sources & evidence

ORD record
ord-2fe8964ce26b4c979f740233fbf48677
Source dataset
uspto-grants-2013_04
Patent number
US08431695B2

Reaction notes

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