Hexane → HCID 178448499, compound

HRID 2206511Notes

Reaction equation

HRID 2206511 reaction equation
[CH:1]([N:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]([C:14]([NH:16][CH2:17][C:18]2[C:19]([OH:26])=[N:20][C:21]([CH3:25])=[CH:22][C:23]=2[CH3:24])=[O:15])=[C:6]1[CH3:27])([CH2:3][CH3:4])[CH3:2].[CH3:28][CH2:29]CCCC>C(O)C>[CH:1]([N:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]([C:14]([NH:16][CH2:17][C:18]2[C:19]([OH:26])=[N:20][C:21]([CH3:25])=[CH:22][C:23]=2[CH3:24])=[O:15])=[C:6]1[CH3:27])([CH2:3][CH3:4])[CH3:2].[CH2:1]([N:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]([C:14]([NH:16][CH2:17][C:18]2[C:19]([OH:26])=[N:20][C:21]([CH3:25])=[CH:22][C:23]=2[CH3:24])=[O:15])=[C:6]1[CH3:27])[CH2:2][CH2:28][CH3:29]

Participants

5

Reactant 2

HCID 8058HexaneHCID 178448499HCID 178448499, compound

Product 2

HCID 178448499HCID 178448499, compoundYield 30%HCID 178448500HCID 178448500, compoundYield 16%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1-sec-butyl-N-((2-hydroxy-4,6-dimethylpyridin-3-yl)methyl)-2-methyl-1H-indole-3-carboxamide (35 mg, 0.1 mmol) was separated by chiral prep-HPLC (Daicel IA (200 mm×20 mm×5 um), hexane: ethanol (0.2% DEA)=70:30, flow rate: 19 mL/min), then (R or S) 1-sec-butyl-N-((2-hydroxy-4,6-dimethylpyridin-3-yl)methyl)-2-methyl-1H-indole-3-carboxamide (11 mg, 30%) and (S or R)-1-sec-butyl-N-((2-hydroxy-4,6-dimethylpyridin-3-yl)methyl)-2-methyl-1H-indole-3-carboxamide (6 mg, 16%) was obtained. The retention times were 8.030 minutes (“Peak 1”; Compound 147) and 14.126 minutes (“Peak 2”; Compound 148) respectively in chiral HPLC chromatography. LRMS (M+H+) m/z: calcd 365.2. found 365. HPLC purity (214 nm): 99%. 1H. NMR (300 MHz, CD3OD): δ 7.73-7.70 (m, 1H), 7.56-7.53 (m, 1H), 7.12-7.09 (m, 2H), 6.11 (s, 1H), 4.54 (s, 3H), 2.64 (s, 3H), 2.43 (s, 3H), 2.25 (s, 3H), 1.97-1.90 (m, 2H), 1.61 (d, J=6.9 Hz, 3H), 0.73 (t, J=7.5 Hz, 3H).

Sources & evidence

ORD record
ord-e1249765f8c34d048066307ef1a2e8f4
Source dataset
uspto-grants-2016_06
Patent number
US09371331B2

Reaction notes

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