Piperidine → HCID 11352433, compound

HRID 2118218Notes

Reaction equation

HRID 2118218 reaction equation
Cl[CH2:2][C:3]([O:5][C:6]1[CH:11]=[CH:10][C:9](/[C:12](/[C:22]2[CH:27]=[CH:26][C:25](/[CH:28]=[CH:29]/[C:30]([OH:32])=[O:31])=[CH:24][CH:23]=2)=[C:13](\[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)/[CH2:14][CH3:15])=[CH:8][CH:7]=1)=[O:4].[NH:33]1[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]1>>[C:16]1(/[C:13](/[CH2:14][CH3:15])=[C:12](/[C:22]2[CH:27]=[CH:26][C:25](/[CH:28]=[CH:29]/[C:30]([OH:32])=[O:31])=[CH:24][CH:23]=2)\[C:9]2[CH:10]=[CH:11][C:6]([O:5][C:3](=[O:4])[CH2:2][N:33]3[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]3)=[CH:7][CH:8]=2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

3

Reactant 2

HCID 8082PiperidineHCID 58877667HCID 58877667, compound

Product 1

HCID 11352433HCID 11352433, compound

Procedure

Treatment of compound 32 with piperidine as described in Example 19 (Step 2) afforded the title compound, 33, as a light yellow solid (85 mg, 77%). 1HNMR (400 MHz, DMSO-d6): δ 0.85 (t, 3H), 1.35 (br, 2H), 1.74 (br, 4H), 2.40 (q, 2H), 3.00 (br, 2H), 3.44 (br, 2H), 4.36 (br, 2H), 6.51 (d, J=16.1 Hz, 1H), 6.87-6.90 (m, 4H), 7.09-7.19 (m, 5H), 7.25 (d, J=8.1 Hz, 2H), 7.58 (d, J=16.1 Hz, 1H), 7.70 (d, J=8.2 Hz, 2H), 10.17 (br, 1H), 12.39 (br, 1H); MS m/z 496 (M+H)+; Anal. calculated for C32H33N1O4.HCl.1.5H2O: C, 68.74; H, 6.67; N, 2.50; Found: C, 68.31; H, 6.34; N, 2.37.

Sources & evidence

ORD record
ord-30ab1727af804f9d86a2bf15353a71fa
Source dataset
uspto-grants-2008_10
Patent number
US07442833B2

Reaction notes

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