Hydrochloric Acid → HCID 24855441, compound

HRID 1616774Notes

Reaction equation

HRID 1616774 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][C:18]#[C:19][CH2:20][CH3:21].C([CH2:25][C:26]([NH:28][C:29]1[CH:37]=[CH:36][CH:35]=[CH:34][C:30]=1[C:31]([OH:33])=[O:32])=[O:27])(O)=O.Cl>C1(C)C=CC=CC=1>[CH2:18]([O:17][C:10]1[CH:11]=[C:12](/[CH:13]=[CH:25]/[C:26]([NH:28][C:29]2[CH:37]=[CH:36][CH:35]=[CH:34][C:30]=2[C:31]([OH:33])=[O:32])=[O:27])[CH:15]=[CH:16][C:9]=1[O:8][CH3:7])[CH2:19][C:20]#[CH:21]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8082PiperidineHCID 4399222-(2-Carboxyacetamido)benzoic acidHCID 86641903HCID 86641903, compound

Product 1

HCID 24855441HCID 24855441, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Piperidine (0.17 mL, 1.7 mmol) was added to a suspension of 4-methoxy-3-(but-1-ynyloxy)benzaldehyde (0.35 g, 1.7 mmol) and 2-[(carboxyacetyl)amino]benzoic acid (0.35 g, 1.6 mmol) in toluene (5 mL) and treated according to Procedure 2, acidifying with 1 M HCl. The crude product was recrystallised from EtOH/water providing (E)-2-[[3-(3-(but-3-ynyloxy)-4-methoxyphenyl)-1-oxo-2-propenyl]amino]benzoic acid (0.40 g, 70%) as a colourless crystalline solid; mp 197-198° C.; δH (400 MHz, DMSO-d6) 2.65 (dt, J=6.8, 2.4 Hz, 2H, CH2CCH), 2.90 (t, J=2.4 Hz, 1H, CCH), 3.80 (s, 3H, OCH3), 4.13 (t, J=6.8 Hz, 2H, OCH2), 6.80 (d, J=15.6 Hz, 1H, CH═CHCO), 7.00 (d, J5′,6′=8.0 Hz, 1H, H5′), 7.16 (t, J3,4=J4,5=8.0 Hz, 1H, H4), 7.26 (d, J5′,6′=8.0 Hz, 1H, H6′), 7.40 (s, 1H, H2′), 7.55 (d, J=15.6 Hz, 1H, CH═CHCO), 7.61 (t, J4,5=J5,6=8.0 Hz, 1H, H5), 7.99 (d, J3,4=8.0 Hz, 1H, H3), 8.61 (d, J5,6=8.0 Hz, 1H, H6), 11.27 (s, 1H, NH), 13.58 (br s, 1H, CO2H); δC (100 MHz, DMSO-d6) 19.0, 55.6, 66.6, 72.5, 81.4, 111.9, 111.9, 116.6, 120.0, 120.3, 122.7, 123.0, 127.3, 131.1, 134.0, 141.0, 141.5, 147.8, 150.7, 164.2, 169.4; HRMS (ESI) calculated for C21H19NO6 [M+H]+ 366.1335. found 366.1337; vmax 753, 1263, 1512, 1581, 1671, 2833, 3250 cm−1.

Workup

  1. additiontreated
  2. customThe crude product was recrystallised from EtOH/water

Sources & evidence

ORD record
ord-24a8ff7cae084da795b34055a0d4c00e
Source dataset
uspto-grants-2014_07
Patent number
US08765812B2

Reaction notes

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