Acetic Acid → HCID 178459259, compound

HRID 1968977Notes

Reaction equation

C([BH3-])#N.[NH2:4][C:5]1[CH:10]=[C:9]([S:11]([CH3:14])(=[O:13])=[O:12])[C:8]([CH3:15])=[CH:7][C:6]=1[OH:16].[CH2:17]([O:20][C@H:21]1[CH2:26][CH2:25][C@H:24]([N:27]2[CH2:32][CH2:31][C:30](=O)[CH2:29][CH2:28]2)[CH2:23][CH2:22]1)[CH2:18][CH3:19].C(O)(=O)C>C1COCC1>[CH3:15][C:8]1[C:9]([S:11]([CH3:14])(=[O:13])=[O:12])=[CH:10][C:5]([NH:4][CH:30]2[CH2:29][CH2:28][N:27]([C@H:24]3[CH2:25][CH2:26][C@H:21]([O:20][CH2:17][CH2:18][CH3:19])[CH2:22][CH2:23]3)[CH2:32][CH2:31]2)=[C:6]([OH:16])[CH:7]=1

Participants

Conditions

Temperature: 100 °C

Procedure

Polymer supported cyanoborohydride (110 mg, 0.47 mmol, 4.3 mmol/g) was added to a solution of 2-amino-5-methyl-4-(methylsulfonyl)phenol (D87, 48 mg, 0.24 mmol), 1-[trans-1-methyl-4-(propyloxy)cyclohexyl]-4-piperidinone (D17, 65 mg, 0.26 mmol, this specific batch contained-25% 1-[trans-4-(propyloxy)cyclohexyl]-4-piperidinone) and acetic acid (0.07 mL, 1.19 mmol) in THF (2.5 mL). The mixture was heated by microwave at 100° C. for 30 min and then for a further 3×30 min. The reaction was then filtered and concentrated by rotary evaporation to give a yellow oil, which was purified by high pH MDAP to give 5-methyl-2-({1-[trans-1-methyl-4-(propyloxy)cyclohexyl]-4-piperidinyl}amino)-4-(methylsulfonyl)phenol (D88, 49 mg, 46%) as a cream solid and 5-methyl-4-(methylsulfonyl)-2-({1-[trans-4-(propyloxy)cyclohexyl]-4-piperidinyl}amino)phenol (D89, 14 mg, 13%) as a yellow oil.

Workup

customfor a further 3×30 min
filtrationThe reaction was then filtered
concentrationconcentrated by rotary evaporation
customto give a yellow oil, which
customwas purified by high pH

Sources & evidence

ORD record: ord-5dfb7d01481448ceb755db4f743debea
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08426443B2

Reaction notes

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