Acetic Acid → HCID 178510110, compound

HRID 909263Notes

Reaction equation

[C:1]([C:3]1[CH:8]=[CH:7][C:6]([S:9]([NH:12][CH:13]2[CH2:18][CH2:17][CH:16]([C:19]([N:21]3[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]3)=[O:20])[CH2:15][CH2:14]2)(=[O:11])=[O:10])=[CH:5][CH:4]=1)#[N:2].[CH:27]1([CH:30]=O)[CH2:29][CH2:28]1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C1COCC1>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([S:9]([NH:12][C@H:13]2[CH2:18][CH2:17][C@H:16]([C:19]([N:21]3[CH2:26][CH2:25][N:24]([CH2:30][CH:27]4[CH2:29][CH2:28]4)[CH2:23][CH2:22]3)=[O:20])[CH2:15][CH2:14]2)(=[O:10])=[O:11])=[CH:7][CH:8]=1)#[N:2]

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 0.1 g (0.26 mmol) 4-cyano-N-[4-(piperazine-1-carbonyl)-cyclohexyl]-benzenesulfonamide, 0.022 g (0.31 mmol) cyclopropanecarboxaldehyde (commercially available), 0.159 g (2.65 mmol) acetic acid and 0.073 g (0.34 mmol) sodium triacetoxyborohydride in 1 mL THF was stirred at 80° C. for 1 h. The mixture was subjected to purification on preparative HPLC eluting with a gradient formed from acetonitrile and water. Evaporation of the product fractions yielded 3 mg (2.6%) of the title compound. MS (m/e): 431.4 (MH+).

Workup

customThe mixture was subjected to purification on preparative HPLC
washeluting with a gradient
customformed from acetonitrile and water
customEvaporation of the product fractions

Sources & evidence

ORD record: ord-0bcf248a9b1a45c683682dd34b343060
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08017773B2

Reaction notes

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