Ethanolamine → 2-[4-(4-Iodo-pyrazol-1-yl)-cyclohexylamino]-ethanol

HRID 1505686Notes

Reaction equation

HRID 1505686 reaction equation
[NH2:1][CH2:2][CH2:3][OH:4].[I:5][C:6]1[CH:7]=[N:8][N:9]([CH:11]2[CH2:16][CH2:15][C:14](=O)[CH2:13][CH2:12]2)[CH:10]=1.[BH4-].[Na+].[OH-].[Na+]>CCO>[I:5][C:6]1[CH:7]=[N:8][N:9]([CH:11]2[CH2:16][CH2:15][CH:14]([NH:1][CH2:2][CH2:3][OH:4])[CH2:13][CH2:12]2)[CH:10]=1

Participants

6

Reactant 4

HCID 700EthanolamineHCID 14798Sodium HydroxideHCID 4311764Sodium borohydrideHCID 595411654-(4-iodo-1H-pyrazol-1-yl)cyclohexanone2×

Product 1

HCID 899244402-[4-(4-Iodo-pyrazol-1-yl)-cyclohexylamino]-ethanolYield 86.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

2-Amino-ethanol (0.30 mL; 4.96 mmol; 1.4 eq.) was added in one portion to a solution of 4-(4-Iodo-pyrazol-1-yl)-cyclohexanone (intermediate 20; 1.00 g; 3.45 mmol; 1.0 eq.) in EtOH. After 1 h the reaction solution was cooled to 0° C. and NaBH4 (290 mg; 7.67 mmol; 2.2 eq.) added portionwise over 1 min. After a further 1 h the reaction suspension was poured into 1 N NaOH solution and extracted with DCM. Combined organic phases were washed with brine, dried over magnesium sulfate, filtered and concentrated. Purification using a SCX-2 cartridge afforded the title compound as a white solid (1.00 g; 84%). 1H NMR (300 MHz, DMSO) δ 7.94 (s, 1H), 7.49 (s, 1H), 4.47 (brs, 1H), 4.12 (m, 1H), 3.45 (m, 2H), 2.60 (t, J=5.8 Hz, 2H), 2.41 (m, 1H), 2.95 (m, 4H), 1.72 (m, 2H), 1.13 (m, 2H).

Workup

  1. extractionextracted with DCM
  2. washCombined organic phases were washed with brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification

Sources & evidence

ORD record
ord-30c243d268bb4206b1f31fdf8cdcfc34
Source dataset
uspto-grants-2015_12
Patent number
US09216991B2

Reaction notes

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