Methanol → HCID 178489766, compound

HRID 1911463Notes

Reaction equation

HRID 1911463 reaction equation
C[Al](C)C.[CH3:5][O:6][C:7]1[CH:8]=[C:9]([CH2:15][CH2:16][C:17]2[CH:18]=[C:19]([NH2:22])[NH:20][N:21]=2)[CH:10]=[C:11]([O:13][CH3:14])[CH:12]=1.[CH3:23][CH:24]([N:26]1[CH2:32][CH2:31][CH2:30][N:29]([C:33]2[S:37][C:36]([C:38](OCC)=[O:39])=[CH:35][CH:34]=2)[CH2:28][CH2:27]1)[CH3:25].CO>C1(C)C=CC=CC=1>[CH3:14][O:13][C:11]1[CH:10]=[C:9]([CH2:15][CH2:16][C:17]2[CH:18]=[C:19]([NH:22][C:38]([C:36]3[S:37][C:33]([N:29]4[CH2:30][CH2:31][CH2:32][N:26]([CH:24]([CH3:25])[CH3:23])[CH2:27][CH2:28]4)=[CH:34][CH:35]=3)=[O:39])[NH:20][N:21]=2)[CH:8]=[C:7]([O:6][CH3:5])[CH:12]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 16682925TrimethylaluminumHCID 66589770HCID 66589770, compoundHCID 178489815HCID 178489815, compound

Product 1

HCID 178489766HCID 178489766, compoundYield 41.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
60 °C

Procedure

Trimethylaluminium (0.751 ml, 1.50 mmol) was added dropwise to a stirred suspension of 5-[2-(3,5-dimethoxyphenyl)ethyl]-2H-pyrazol-3-amine (148 mg, 0.60 mmol) and ethyl 5-(4-propan-2-yl-1,4-diazepan-1-yl)thiophene-2-carboxylate (178 mg, 0.60 mmol) in toluene (3.002 ml) at 25° C. The resulting solution was stirred at 60° C. for 18 h. The cooled reaction mixture was added to methanol (50 mL) and treated with HCL (2M aqueous solution, to pH7 or below) and purified by ion exchange chromatography, using a SCX column. The desired product was eluted from the column using 7M NH3/MeOH and evaporated to dryness to afford impure material. The crude product was purified by preparative HPLC, using decreasingly polar mixtures of water (containing 1% NH3) and MeCN as eluents. Fractions containing the desired compound were evaporated to dryness to afford the title compound (123 mg, 41%) as a yellow solid.

Workup

  1. customThe cooled reaction mixture
  2. custompurified by ion exchange chromatography
  3. washThe desired product was eluted from the column
  4. customevaporated to dryness
  5. customto afford impure material
  6. customThe crude product was purified by preparative HPLC
  7. additionFractions containing the desired compound
  8. customwere evaporated to dryness

Sources & evidence

ORD record
ord-eb43c43944d44cafa513cb7730d6b831
Source dataset
uspto-grants-2013_12
Patent number
US08604022B2

Reaction notes

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