Diisopropylethylamine → HCID 66990871, compound

HRID 2367253Notes

Reaction equation

HRID 2367253 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.[Cl:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[CH2:29][CH2:30][NH2:31].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:24]4[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=4[Cl:22])[CH:5]=3)=[CH:9][CH:10]=2)[NH:14][N:13]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 831172-(2-Chlorophenyl)ethylamineHCID 58504757HCID 58504757, compound

Product 1

HCID 66990871HCID 66990871, compoundYield 39.9%

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-(2-chlorophenyl)ethanamine (300 mg, 1.94 mmol), and Hunig's base (2 mL) in NMP (3 mL) was heated for 2 hours at 160° 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 to afford the title compound (150 mg) as a yellow solid. 1H NMR (400 MHz, DMSO-d6): δ 2.99 (t, J=8 Hz, 2H), 3.52-3.53 (m, 2H), 5.39 (s, 2H), 6.03 (s, 2H), 6.29 (s, 1H), 7.03 (s, 1H), 7.24-7.46 (m, 5H), 7.71 (d, J=8.0 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-0dce65f07c97418fbdd8f7997eea34a9
Source dataset
uspto-grants-2014_04
Patent number
US08697685B2

Reaction notes

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