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Cyclohexylamine → HCID 18446572, compound

HRID 1868331
Notes
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Reaction equation

HRID 1868331 reaction equation
Cl[C:2]1[C:7]2[CH:8]=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([C:17]([CH3:20])([CH3:19])[CH3:18])=[CH:13][CH:12]=3)[S:10][C:6]=2[C:5]([C:21]#[N:22])=[CH:4][N:3]=1.[CH:23]1([NH2:29])[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH:23]1([NH:29][C:2]2[C:7]3[CH:8]=[C:9]([C:11]4[CH:16]=[CH:15][C:14]([C:17]([CH3:18])([CH3:20])[CH3:19])=[CH:13][CH:12]=4)[S:10][C:6]=3[C:5]([C:21]#[N:22])=[CH:4][N:3]=2)[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 7965CyclohexylamineHCID 11430Potassium CarbonateHCID 18446571HCID 18446571, compound

Product 1

HCID 18446572HCID 18446572, compoundYield 70.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 4-chloro-7-cyano-2-(4′-t-butylphenyl)-thieno[3,2-c]pyridine (0.05 g, 0.153 mmol) in DMF was added cyclohexylamine (0.017 g, 0.168 mmol) and potassium carbonate (0.023 g, 0.168 mmol). The resulting mixture was stirred under nitrogen at 80° C. for 2 h. After this time the mixture was partitioned between ethyl acetate (10 mL) and saturated aqueous sodium bicarbonate solution (10 mL), and the organic layer washed with water and brine, then dried over magnesium sulphate and concentrated under reduced pressure. Purification by silica gel chromatography (eluent 20% ethyl acetate in hexane) afforded 0.042 g of 102. 1H NMR (400 MHz, CDCl3) δ 8.27 (s, 1H), 7.63 (d, 2H), 7.50 (d, 2H), 7.38 (s, 1H), 5.14 (bs, 1H), 4.20 (bs, 1H), 2.18 (m, 2H), 1.80 (m, 4H), 1.6-1.12 (m, 13H).

Workup

  1. customAfter this time the mixture was partitioned between ethyl acetate (10 mL) and saturated aqueous sodium bicarbonate solution (10 mL)
  2. washthe organic layer washed with water and brine
  3. dry with materialdried over magnesium sulphate
  4. concentrationconcentrated under reduced pressure
  5. customPurification by silica gel chromatography (eluent 20% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-bc022de74c424f57998adcaf49bb0208
Source dataset
uspto-grants-2009_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07635695B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes