N-Methylbenzeneethanamine → HCID 58504481, compound

HRID 2367251Notes

Reaction equation

HRID 2367251 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.[CH3:22][NH:23][CH2:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.CCN(C(C)C)C(C)C>CN1C(=O)CCC1>[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]([N:23]([CH3:22])[CH2:24][CH2:25][C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)[CH:5]=3)=[CH:9][CH:10]=2)[NH:14][N:13]=1

Participants

5

Reactant 3

HCID 11503N-MethylbenzeneethanamineHCID 81531DiisopropylethylamineHCID 58504757HCID 58504757, compound

Product 1

HCID 58504481HCID 58504481, compoundYield 14.1%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
160 °C

Procedure

A mixture of 6-[2-amino-6-(methylsulfonyl)-4-pyrimidinyl]-1H-indazol-3-amine (300 mg, 0.99 mmol), N-methyl-2-phenylethanamine (300 mg, 2.22 mmol), and Hunig's base (2 mL) in NMP (3 mL) was heated for 2 hours at 160° C. for 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 to afford the title compound (50 mg) as a yellow solid. LC-MS (ES) m/z=360 [M+H]+. 1H NMR (400 MHz, DMSO-d6): δ 2.85 (t, J=7.6 Hz, 2H), 3.0 (s, 3H), 3.76 (t, J=7.6 Hz, 2H), 5.37 (s, 2H), 6.04 (s, 2H), 6.39 (s, 1H), 7.19-7.23 (m, 1H), 7.30-7.32 (m, 4H), 7.53 (d, J=8.4 Hz, 1H), 7.71 (d, J=8.8 Hz, 1H), 7.91 (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

Sources & evidence

ORD record
ord-48dc39b23d4b4bad95fcb0440de6fb7c
Source dataset
uspto-grants-2014_04
Patent number
US08697685B2

Reaction notes

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