Cyclopropylamine → HCID 66991312, compound

HRID 2367246Notes

Reaction equation

HRID 2367246 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([C:8]2[CH:16]=[C:15]3[C:11]([C:12]([NH2:17])=[N:13][NH:14]3)=[CH:10][CH:9]=2)[CH:5]=[C:4](S(C)(=O)=O)[N:3]=1.[CH:22]1([NH2:25])[CH2:24][CH2:23]1.CCN(C(C)C)C(C)C>O1CCOCC1>[NH2:17][C:12]1[C:11]2[C:15](=[CH:16][C:8]([C:6]3[N:7]=[C:2]([NH2:1])[N:3]=[C:4]([NH:25][CH:22]4[CH2:24][CH2:23]4)[CH:5]=3)=[CH:9][CH:10]=2)[NH:14][N:13]=1

Participants

5

Reactant 3

HCID 69828CyclopropylamineHCID 81531DiisopropylethylamineHCID 58504757HCID 58504757, compound

Product 1

HCID 66991312HCID 66991312, compoundYield 5.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 6-[2-amino-6-(methylsulfonyl)-4-pyrimidinyl]-1H-indazol-3-amine (650 mg, 2.14 mmol), cyclopropylamine (650 mg, 11.4 mmol), and Hunig's base (2 mL, 11.4 mmol) in 1,4-dioxane (5 mL) was heated for 2 hours at 120° C. in a BiotageInitiator® microwave synthesizer. Upon cooling, the mixture was decanted to remove the solids, and the resulting solution was concentrated to dryness. The crude material was purified by RPHPLC (gradient: 15% CH3CN/H2O to 45% CH3CN/H2O) to afford the title compound (32 mg) as a yellow solid. LC-MS (ES) m/z=282 [M+H]+. 1H NMR (400 MHz, DMSO-d6): δ 0.46-0.49 (m, 2H), 0.73 (t, J=6.8 Hz, 2H), 2.62-2.67 (m, 1H), 5.37 (s, 2H), 6.0 (s, 2H), 6.38 (s, 1H), 7.02 (s, 1H), 7.45 (d, J=8.8 Hz, 1H), 7.70 (d, J=8.0 Hz, 1H), 7.86 (s, 1H), 11.50 (s, 1H).

Workup

  1. temperatureUpon cooling
  2. customthe mixture was decanted
  3. customto remove the solids
  4. concentrationthe resulting solution was concentrated to dryness
  5. customThe crude material was purified by RPHPLC (gradient: 15% CH3CN/H2O to 45% CH3CN/H2O)

Sources & evidence

ORD record
ord-cf9c18ee5aeb493ca12f61d5fbbbc836
Source dataset
uspto-grants-2014_04
Patent number
US08697685B2

Reaction notes

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