3-Phenylpropylamine → HCID 66991236, compound

HRID 2367247Notes

Reaction equation

HRID 2367247 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.[C:22]1([CH2:28][CH2:29][CH2:30][NH2:31])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.CCN(C(C)C)C(C)C>>[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][CH2:28][C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)[CH:5]=3)=[CH:9][CH:10]=2)[NH:14][N:13]=1

Participants

4

Reactant 3

HCID 162593-PhenylpropylamineHCID 81531DiisopropylethylamineHCID 58504757HCID 58504757, compound

Product 1

HCID 66991236HCID 66991236, compoundYield 15.3%

Conditions

Temperature
140 °C

Procedure

A mixture of 6-[2-amino-6-(methylsulfonyl)-4-pyrimidinyl]-1H-indazol-3-amine (500 mg, 1.64 mmol), (3-phenylpropyl)amine (500 mg, 3.70 mmol), and Hunig's base (2 mL) in 1-1-methyl-2-pyrrolidinone (NMP) (3 mL) was heated for 4 hours at 140° 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: 10% CH3CN/H2O to 30% CH3CN/H2O) to afford the title compound (90 mg) as a yellow solid. LC-MS (ES) m/z=360 [M+H]+. 1H NMR (400 MHz, DMSO-d6): δ 1.80-1.87 (m, 2H), 2.64-2.68 (m, 2H), 3.28-3.30 (m, 2H), 5.37 (s, 2H), 5.97 (s, 2H), 6.27 (s, 1H), 6.93 (s, 1H), 7.17-7.31 (m, 5H), 7.40 (d, J=8.4 Hz, 1H), 7.70 (d, J=8.0 Hz, 1H), 7.84 (s, 1H), 11.51 (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: 10% CH3CN/H2O to 30% CH3CN/H2O)

Sources & evidence

ORD record
ord-d4984f786fb744d5b2126f40268d5a36
Source dataset
uspto-grants-2014_04
Patent number
US08697685B2

Reaction notes

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