2-Morpholinoethylamine → HCID 68514419, compound

HRID 2241436Notes

Reaction equation

HRID 2241436 reaction equation
[CH3:1][O:2][C:3]1[CH:19]=[CH:18][C:6]([CH2:7][N:8]2[C:12]3=[N:13][CH:14]=[CH:15][C:16](Cl)=[C:11]3[CH:10]=[N:9]2)=[CH:5][CH:4]=1.[O:20]1[CH2:25][CH2:24][N:23]([CH2:26][CH2:27][NH2:28])[CH2:22][CH2:21]1>CN1C(=O)CCC1.CCOC(C)=O>[CH3:1][O:2][C:3]1[CH:19]=[CH:18][C:6]([CH2:7][N:8]2[C:12]3[N:13]=[CH:14][CH:15]=[C:16]([NH:28][CH2:27][CH2:26][N:23]4[CH2:24][CH2:25][O:20][CH2:21][CH2:22]4)[C:11]=3[CH:10]=[N:9]2)=[CH:5][CH:4]=1

Participants

5

Reactant 2

HCID 4082852-MorpholinoethylamineHCID 593985764-chloro-1-(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridine

Product 1

HCID 68514419HCID 68514419, compoundYield 56.2%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
150 °C

Procedure

1-(4-methoxybenzyl)-4-chloro-1H-pyrazolo[3,4-b]pyridine (0.200 g, 0.731 mmol) was charged to a pressure tube in 5 mL of NMP. 2-morpholinoethanamine (0.144 ml, 1.10 mmol) was added and the reaction was heated to 150° C. for 72 hours. After cooling, the reaction mixture was diluted with 25 mL of EtOAc and washed with water (2×15 mL) and then dried with brine and Na2SO4. Purification via flash Si 10 g eluting with 1-5% MeOH/DCM with NH4OH to afford 151 mg (55%) of product as a yellow oil. 1H NMR (400 MHz, CDCl3) δ 8.20 (d, 1H), 7.92 (s, 1H), 7.30 (t, 2H), 6.83 (m, 2H), 6.14 (d, 1H), 5.56 (s, 2H), 5.41 (s, 1H), 3.75 (m, 7H), 3.44 (m, 2H), 2.73 (t, 2H), 2.51 (bs, 4H).

Workup

  1. temperatureAfter cooling
  2. washwashed with water (2×15 mL)
  3. dry with materialdried with brine and Na2SO4
  4. customPurification via flash Si 10 g
  5. washeluting with 1-5% MeOH/DCM with NH4OH

Sources & evidence

ORD record
ord-fbff6b3aff4b4f0180c3047b7cb5a1bc
Source dataset
uspto-grants-2010_05
Patent number
US07723330B2

Reaction notes

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