Acetic Acid → HCID 24855267, compound

HRID 1616748Notes

Reaction equation

HRID 1616748 reaction equation
N1CCCCC1.[CH3:7][O:8][C:9]1[CH:16]=[CH:15][C:12]([CH:13]=O)=[CH:11][C:10]=1[O:17][CH2:18][C:19]#[C:20][CH2:21][CH3:22].C([CH2:26][C:27]([NH:29][C:30]1[CH:38]=[CH:37][CH:36]=[CH:35][C:31]=1[C:32]([OH:34])=[O:33])=[O:28])(O)=O.CC(O)=O>C1(C)C=CC=CC=1>[CH3:7][O:8][C:9]1[CH:16]=[CH:15][C:12](/[CH:13]=[CH:26]/[C:27]([NH:29][C:30]2[CH:38]=[CH:37][CH:36]=[CH:35][C:31]=2[C:32]([OH:34])=[O:33])=[O:28])=[CH:11][C:10]=1[O:17][CH2:18][C:19]#[C:20][CH2:21][CH3:22]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 8082PiperidineHCID 4399222-(2-Carboxyacetamido)benzoic acidHCID 59333855HCID 59333855, compound

Product 1

HCID 24855267HCID 24855267, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Piperidine (0.24 mL, 2.5 mmol) was added to a suspension of 4-methoxy-3-(pent-2-ynyl)oxybenzaldehyde (0.54 g, 2.5 mmol) and 2-[(carboxyacetyl)amino]benzoic acid (0.53 g, 2.4 mmol) in toluene (5.0 mL) and treated according to Procedure 2, acidifying with 20% AcOH. (E)-2-[[3-(4-Methoxy-3-(pent-2-ynyloxy)phenyl)-1-oxo-2-propenyl]amino]benzoic acid (0.50 g, 60%) was obtained as a yellow crystalline solid; mp 124-125° C.; δH (400 MHz, DMSO-d6) 1.06 (t, J=7.4 Hz, 2H, CH2CH3), 2.23 (q, J=7.4 Hz, 3H, CH2CH3), 3.80 (s, 3H, OCH3), 4.81 (s, 2H, OCH2), 6.73 (d, J=15.6 Hz, 1H, CH═CHCO), 7.01 (d, J5′,6′=8.4 Hz, 1H, H5′), 7.16 (t, J3,4=J4,5=8.0 Hz, 1H, H4), 7.28 (dd, J5′,6′=8.4, J2′,6′=1.6 Hz, 1H, H6′), 7.42 (d, J2′,6′=1.6 Hz, 1H, H2′), 7.57 (d, J=15.6 Hz, 1H, CH═CHCO), 7.61 (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), 11.31 (s, 1H, NH), 13.59 (br s, 1H, CO2H); δC (100 MHz, DMSO-d6) 11.7, 13.6, 55.6, 56.6, 74.9, 89.3, 111.9, 112.5, 116.5, 119.9, 120.3, 122.7, 123.3, 127.0, 131.1, 134.0, 141.1, 141.6, 146.8, 151.0, 164.1, 169.5; HRMS (ESI) calculated for C22H21NO6 [M+Na]+ 402.1312. found 402.1317; vmax 753, 1015, 1257, 1506, 1584, 1659, 2920, 3246, 3520 cm−1.

Workup

  1. additiontreated

Sources & evidence

ORD record
ord-56e1eece07c44bebba1420dfc4c6ebc7
Source dataset
uspto-grants-2014_07
Patent number
US08765812B2

Reaction notes

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