Ethanol → HCID 178507380, compound

HRID 1946996Notes

Reaction equation

HRID 1946996 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[CH:6]=[CH:7][N:8]2[C:13]1[CH:18]=[CH:17][N:16]=[C:15]([NH:19][C@H:20]2[CH2:25][CH2:24][C@H:23]([OH:26])[CH2:22][CH2:21]2)[N:14]=1)([O-])=O.CCO.[Cl-].[NH4+]>[Fe].O>[NH2:1][C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[CH:6]=[CH:7][N:8]2[C:13]1[CH:18]=[CH:17][N:16]=[C:15]([NH:19][C@H:20]2[CH2:21][CH2:22][C@H:23]([OH:26])[CH2:24][CH2:25]2)[N:14]=1

Participants

6

Reactant 3

HCID 702EthanolHCID 25517Ammonium ChlorideHCID 178526508HCID 178526508, compound

Product 1

HCID 178507380HCID 178507380, compound

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of trans-4-[4-(4-nitroindol-1-yl)-pyrimidin-2-ylamino]-cyclohexanol (2.44 g), EtOH (35 mL) and water (11 mL) was heated to 80° C. To the hot suspension was added ammonium chloride (1.46 g) followed by iron(0) (Fisher, 1.55 g) and the resulting mixture heated to 80° C. for 2 h, then to 50° C. for an additional 24 h. The reaction mixture was filtered through a CELITE™ pad, the filter cake washed with EtOAc/MeOH (3:2), and the filtrate evaporated under reduced pressure. The crude residue was purified by flash chromatography (MeOH/DCM, gradient from 2.5:97.5 to 10:90) to give trans-4-[4-(4-aminoindol-1-yl)-pyrimidin-2-ylamino]-cyclohexanol as a light yellow solid. MS=324 [M+H]+; MP=218.9-220.1° C.

Workup

  1. temperaturethe resulting mixture heated to 80° C. for 2 h
  2. filtrationThe reaction mixture was filtered through a CELITE™ pad
  3. washthe filter cake washed with EtOAc/MeOH (3:2)
  4. customthe filtrate evaporated under reduced pressure
  5. customThe crude residue was purified by flash chromatography (MeOH/DCM, gradient from 2.5:97.5 to 10:90)

Sources & evidence

ORD record
ord-57b8bb5038a14ce19eca11d64c993530
Source dataset
uspto-grants-2013_03
Patent number
US08399462B2

Reaction notes

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