Acetic Acid → HCID 24855219, compound

HRID 1616746Notes

Reaction equation

HRID 1616746 reaction equation
N1CCCCC1.[CH3:7][O:8][C:9]1[CH:10]=[C:11]([CH:14]=[CH:15][C:16]=1[O:17][CH2:18][C:19]#[C:20][CH2:21][CH3:22])[CH:12]=O.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:10]=[C:11](/[CH:12]=[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:14]=[CH:15][C:16]=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 59333872HCID 59333872, compound

Product 1

HCID 24855219HCID 24855219, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Piperidine (0.22 mL, 2.2 mmol) was added to a suspension of 3-methoxy-4-(pent-2-ynyl)oxybenzaldehyde (0.50 g, 2.3 mmol) and 2-[(carboxyacetyl)amino]benzoic acid (0.49 g, 2.2 mmol) in toluene (5.0 mL) and treated according to Procedure 2, acidifying with 20% AcOH. (E)-2-[[3-(3-Methoxy-4-(pent-2-ynyloxy)phenyl)-1-oxo-2-propenyl]amino]benzoic acid (0.50 g, 60%) was obtained as a colourless crystalline solid; mp 185.5-186.5° C.; δH (400 MHz, DMSO-d6) 1.05 (t, J=7.4 Hz, 2H, CH2CH3), 2.20 (q, J=7.4 Hz, 3H, CH2CH3), 3.84 (s, 3H, OCH3), 4.78 (s, 2H, OCH2), 6.80 (d, J=15.6 Hz, 1H, CH═CHCO), 7.03 (d, J5′,6′=8.4 Hz, 1H, H5′), 7.16 (t, J3,4=J4,5 8.0 Hz, 1H, H4), 7.24 (d, J5′,6′=8.4 Hz, 1H, H6′), 7.39 (s, 1H, H2′), 7.56 (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), 13.53 (br s, 1H, CO2H); δC (100 MHz, DMSO-d6) 11.7, 13.5, 56.6, 56.4, 74.7, 89.3, 110.7, 113.3, 116.6, 120.2, 120.3, 122.2, 122.7, 127.9, 131.1, 134.0, 141.0, 141.5, 148.5, 149.2, 164.1, 169.5; HRMS (ESI) calculated for C22H21NO6 [M+Na]+ 402.1312. found 402.1317; vmax 747, 1001, 1253, 1508, 1583, 1661, 2980, 3246, 3523 cm−1.

Workup

  1. additiontreated

Sources & evidence

ORD record
ord-60fb2a0d9c4a4d8b879a548fa8aff999
Source dataset
uspto-grants-2014_07
Patent number
US08765812B2

Reaction notes

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