Dimethylformamide dimethyl acetal → HCID 86616471, compound

HRID 1864804Notes

Reaction equation

[F:1][C:2]1[CH:35]=[CH:34][C:5]([C:6]([N:8]([CH2:16][C:17]2[CH:22]=[C:21]([C:23]3[CH:28]=[C:27]([CH3:29])[C:26]([N+:30]([O-:32])=[O:31])=[CH:25][N:24]=3)[CH:20]=[CH:19][C:18]=2[F:33])[CH2:9][CH2:10][N:11]2[CH2:15][CH2:14][CH2:13][CH2:12]2)=[O:7])=[CH:4][CH:3]=1.CO[CH:38](OC)[N:39]([CH3:41])[CH3:40]>CN(C)C=O>[CH3:38][N:39]([CH3:41])/[CH:40]=[CH:29]/[C:27]1[C:26]([N+:30]([O-:32])=[O:31])=[CH:25][N:24]=[C:23]([C:21]2[CH:20]=[CH:19][C:18]([F:33])=[C:17]([CH:22]=2)[CH2:16][N:8]([CH2:9][CH2:10][N:11]2[CH2:12][CH2:13][CH2:14][CH2:15]2)[C:6](=[O:7])[C:5]2[CH:34]=[CH:35][C:2]([F:1])=[CH:3][CH:4]=2)[CH:28]=1

Participants

Conditions

Temperature: 80 °C

Procedure

4-Fluoro-N-[2-fluoro-5-(4-methyl-5-nitro-pyridin-2-yl)-benzyl]-N-(2-pyrrolidin-1-yl-ethyl)-benzamide (prepared according to example 20, 600 mg, 1.25 mmol) in 15 mL of dimethylformamide was treated with dimethylformamide dimethyl acetal (0.23 mL, 1.68 mmol), and the resulting mixture was heated at 80° C. for 5 h. The mixture was allowed to cool and the volatiles were removed. The residue was partitioned between ethyl acetate and water. The organic phase was washed with water, dried over MgSO4, filtered and evaporated to give an oil. The above process was repeated to give 485 mg of product.

Workup

temperatureto cool
customthe volatiles were removed
customThe residue was partitioned between ethyl acetate and water
washThe organic phase was washed with water
dry with materialdried over MgSO4
filtrationfiltered
customevaporated
customto give an oil

Sources & evidence

ORD record: ord-133ed32b9bec43b39ff8bfdccca9a8ec
Source dataset: uspto-grants-2009_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07625889B2

Reaction notes

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