Hydrochloric Acid → HCID 24855270, compound

HRID 1616757Notes

Reaction equation

HRID 1616757 reaction equation
N1CCCCC1.[CH:7]1([O:13][C:14]2[CH:21]=[CH:20][C:17]([CH:18]=O)=[CH:16][C:15]=2[O:22][CH3:23])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1.C([CH2:27][C:28]([NH:30][C:31]1[CH:39]=[CH:38][CH:37]=[CH:36][C:32]=1[C:33]([OH:35])=[O:34])=[O:29])(O)=O.Cl>C1(C)C=CC=CC=1.CCO.O>[CH:7]1([O:13][C:14]2[CH:21]=[CH:20][C:17](/[CH:18]=[CH:27]/[C:28]([NH:30][C:31]3[CH:39]=[CH:38][CH:37]=[CH:36][C:32]=3[C:33]([OH:35])=[O:34])=[O:29])=[CH:16][C:15]=2[O:22][CH3:23])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8082PiperidineHCID 4399222-(2-Carboxyacetamido)benzoic acidHCID 22022329HCID 22022329, compound

Product 1

HCID 24855270HCID 24855270, compoundYield 60.4%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 19096565Water ethanolSolvent

Procedure

Piperidine (0.45 mL, 4.5 mmol) was added to a suspension of 4-cyclohexyloxy-3-methoxybenzaldehyde (1.06 g, 4.54 mmol) and 2-[(carboxyacetyl)amino]benzoic acid (0.92 g, 4.1 mmol) in toluene (5.0 mL) and treated according to Procedure 2, acidifying with 1 M HCl. The crude product was recystallised from EtOH/water providing (E)-2-{[3-(4-cyclohexyloxy-3-methoxyphenyl)-1-oxo-2-propenyl]amino}benzoic acid (0.98 g, 60%) as a colourless crystalline solid; mp 90-92° C.; δH (400 MHz, DMSO-d6) 1.25-1.52 (m, 6H, CH2), 1.70 (m, 2H, CH2), 1.89 (m, 2H, CH2), 3.82 (s, 3H, OCH3), 4.33 (m, 1H, OCH), 6.76 (d, J=15.6 Hz, 1H, CH═CHCO), 6.99 (d, J5′,6′=8.4 Hz, 1H, H5′), 7.15 (t, =J3,4=J4,6=8.0 Hz, 1H, H4), 7.19 (d, J5,6=8.4 Hz, 1H, H6′), 7.35 (s, 1H, H2′), 7.55 (d, J=15.6 Hz, 1H, CH═CHCO), 7.60 (t, J4,5=J5,6=8.0 Hz, 1H, H5), 8.00 (d, J3,4=8.0 Hz, 1H, H3), 8.62 (d, J5,6=8.0 Hz, 1H, H6), 11.29 (s, 1H, NH), 13.56 (br s, 1H, CO2H); δC (100 MHz, DMSO-d6) 23.2, 25.1, 31.4, 55.7, 79.4, 111.2, 114.8, 116.6, 119.8, 120.3, 122.4, 122.6, 127.3, 131.1, 134.0, 141.1, 141.6, 148.6, 150.0, 164.2, 169.5; HRMS (ESI) calculated for C23H25NO5 [M+Na]+ 418.1625. found 418.1625; vmax 745, 1259, 1504, 1588, 1659, 2929, 3520 cm−1.

Workup

  1. additiontreated

Sources & evidence

ORD record
ord-fb15c3a259b24c25bb96c09e894ce5fe
Source dataset
uspto-grants-2014_07
Patent number
US08765812B2

Reaction notes

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