Trimethylaluminum → HCID 178489763, compound

HRID 16844Notes

Reaction equation

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

Participants

Conditions

Temperature: 60 °C

Procedure

Ethyl 5-(4-methyl-1,4-diazepan-1-yl)thiophene-2-carboxylate (0.201 g, 0.75 mmol) and 5-[2-(3,5-dimethoxyphenyl)ethyl]-2H-pyrazol-3-amine (0.185 g, 0.75 mmol) in toluene (10 mL) were stirred at 20° C. and a 2M solution of trimethylaluminium in toluene (0.938 mL, 1.88 mmol) was added drop-wise. The reaction stirred under nitrogen at 60° C. for 18 h. The reaction mixture was cooled and quenched by pouring into methanol (50 ml), acidified with few drops of 2N hydrochloric acid. The crude product was purified by ion exchange chromatography, using a SCX column. The desired product was eluted from the column using 7M NH3/MeOH and fractions were evaporated to dryness to afford crude product.

Workup

temperatureThe reaction mixture was cooled
customquenched
additionby pouring into methanol (50 ml)
customThe crude product was purified by ion exchange chromatography
washThe desired product was eluted from the column
customwere evaporated to dryness
customto afford crude product

Sources & evidence

ORD record: ord-f0b7fadadc9f4ac3b82bf5c98c40fb1c
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07737149B2

Reaction notes

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