Diisopropylethylamine → HCID 71611138, compound

HRID 2409066Notes

Reaction equation

HRID 2409066 reaction equation
[NH:1]1[C:5]2=[CH:6][N:7]=[CH:8][C:9]([CH2:10][NH2:11])=[C:4]2[CH:3]=[CH:2]1.Cl[C:13]1[N:18]=[C:17]([NH:19][C:20]2[CH:24]=[C:23]([CH:25]3[CH2:27][CH2:26]3)[NH:22][N:21]=2)[CH:16]=[CH:15][N:14]=1.CCN(C(C)C)C(C)C>CC(O)C>[NH:1]1[C:5]2=[CH:6][N:7]=[CH:8][C:9]([CH2:10][NH:11][C:13]3[N:18]=[C:17]([NH:19][C:20]4[CH:24]=[C:23]([CH:25]5[CH2:27][CH2:26]5)[NH:22][N:21]=4)[CH:16]=[CH:15][N:14]=3)=[C:4]2[CH:3]=[CH:2]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 581691182-chloro-N-(5-cyclopropyl-1H-pyrazol-3-yl)pyrimidin-4-amineHCID 82417690HCID 82417690, compound

Product 1

HCID 71611138HCID 71611138, compoundYield 11.1%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of (1H-pyrrolo[2,3-c]pyridin-4-yl)methanamine (236 mg, 1.61 mmol), 2-chloro-N-(5-cyclopropyl-1H-pyrazol-3-yl)pyrimidin-4-amine (344 mg, 1.46 mmol) and DIPEA (565 mg, 4.38 mmol) in IPA (2 mL) was stirred in a sealed tube at 120° C. for 18 h. The reaction mixture was cooled to RT and concentrated in vacuo. The crude residue was purification by preparative HPLC to afford 56 mg (11.1%) of the title compound as white solid: 1H NMR (500 MHz, CD3OD) δ 8.64 (s, 1H), 8.06 (s, 1H), 7.85 (s, 1H), 7.59 (d, J=3.0, 1H), 6.72 (d, J=3.0, 1H), 6.17-5.96 (m, 2H), 4.92 (s, 2H), 1.75 (s, 1H), 0.85 (d, J=4.5, 2H), 0.51 (s, 2H); MS (ESI) m/z: 347.2 [M+1]+.

Workup

  1. temperatureThe reaction mixture was cooled to RT
  2. concentrationconcentrated in vacuo
  3. custompurification by preparative HPLC

Sources & evidence

ORD record
ord-1058306697244322888a95bf3c0a41ef
Source dataset
uspto-grants-2014_08
Patent number
US08815877B2

Reaction notes

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