Diisopropylethylamine → HCID 66990712, compound

HRID 2367250Notes

Reaction equation

HRID 2367250 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)C=C(S(C)(=O)=O)[N:3]=1.[Cl:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1CCN.CC[N:34]([CH:38]([CH3:40])C)[CH:35]([CH3:37])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:38]([NH:34][CH2:35][CH2:37][C:25]4[CH:26]=[CH:27][CH:28]=[C:23]([Cl:22])[CH:24]=4)[CH:40]=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 66990712HCID 66990712, compound

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 (120 mg) as a yellow solid. 1H NMR (400 MHz, DMSO-d6): δ 2.87 (t, J=7.2 Hz, 2H), 3.52-3.54 (m, 2H), 5.39 (s, 2H),), 6.05 (s, 2H), 6.29 (s, 1H), 6.97 (s, 1H), 7.25-7.44 (m, 5H), 7.71 (d, J=8.4 Hz, 1H), 7.86 (s, 1H), 11.54 (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-c8ff95fc85d74f43a72da026f2348967
Source dataset
uspto-grants-2014_04
Patent number
US08697685B2

Reaction notes

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