Diisopropylethylamine → HCID 66990780, compound

HRID 2367252Notes

Reaction equation

HRID 2367252 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.[F:22][C:23]1[CH:24]=[C:25]([CH2:29][CH2:30][NH2:31])[CH:26]=[CH:27][CH:28]=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]([NH:31][CH2:30][CH2:29][C:25]4[CH:26]=[CH:27][CH:28]=[C:23]([F:22])[CH:24]=4)[CH:5]=3)=[CH:9][CH:10]=2)[NH:14][N:13]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 5339282-(3-Fluorophenyl)ethanamineHCID 58504757HCID 58504757, compound

Product 1

HCID 66990780HCID 66990780, compoundYield 44.5%

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), 2-(3-fluorophenyl)ethanamine (300 mg, 2.16 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 (160 mg) as a yellow solid. LC-MS (ES) m/z=364 [M+H]+. 1H NMR (400 MHz, DMSO-d6): δ 2.86-2.90 (m, 2H), 3.51-3.56 (m, 2H), 5.39 (s, 2H), 6.04 (s, 2H), 6.29 (s, 1H), 6.97-7.43 (m, 6H), 7.70 (d, J=8.4 Hz, 1H), 7.85 (s, 1H), 11.53 (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-6b1afe4ef71e41d68b213315a0356d01
Source dataset
uspto-grants-2014_04
Patent number
US08697685B2

Reaction notes

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