10258-71-6 → HCID 24855380, compound

HRID 1616749Notes

Reaction equation

HRID 1616749 reaction equation
O=C1O[C@H]([C@H](CO)O)C([O-])=C1O.[Na+].[CH3:14][O:15][C:16]1[CH:17]=[C:18](/[CH:26]=[CH:27]/[C:28]([NH:30][C:31]2[CH:39]=[CH:38][CH:37]=[CH:36][C:32]=2[C:33]([OH:35])=[O:34])=[O:29])[CH:19]=[CH:20][C:21]=1[O:22][CH2:23][C:24]#[CH:25].[N:40]([CH2:43][C:44]([NH:46][C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1)=[O:45])=[N+:41]=[N-:42]>CS(C)=O.O.S([O-])([O-])(=O)=O.[Cu+2].C(C(N(C(C1N=NNC=1)CC1C=CC=CC=1)C(C1N=NNC=1)CC1C=CC=CC=1)C1N=NNC=1)C1C=CC=CC=1>[CH3:14][O:15][C:16]1[CH:17]=[C:18](/[CH:26]=[CH:27]/[C:28]([NH:30][C:31]2[CH:39]=[CH:38][CH:37]=[CH:36][C:32]=2[C:33]([OH:35])=[O:34])=[O:29])[CH:19]=[CH:20][C:21]=1[O:22][CH2:23][C:24]1[N:42]=[N:41][N:40]([CH2:43][C:44](=[O:45])[NH:46][C:47]2[CH:48]=[CH:49][CH:50]=[CH:51][CH:52]=2)[CH:25]=1

Participants

8

Reactant 3

HCID 1420110110258-71-6HCID 23648966SHP-627HCID 23667548Sodium Ascorbate

Product 1

HCID 24855380HCID 24855380, compoundYield 81.2%

Reagents, catalysts & solvents 4

HCID 24462Copper SulfateCatalystHCID 178420222HCID 178420222, compoundCatalystHCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent2×

Procedure

Sodium ascorbate (28 mg, 140 μmol), tris-(benzyltriazolylmethyl)amine (15 mg, 28 μmol) and copper sulfate (4.5 mg, 28 μmol) were added to a solution of (E)-2-[[3-(3-methoxy-4-propargyloxyphenyl)-1-oxo-2-propenyl]amino]benzoic acid (0.50 g, 1.4 mmol) and 2-azido-N-phenylacetamide (0.25 g, 1.4 mmol) in DMSO (20 mL) and water (5.0 mL). The solution was stirred at rt for 16 h and diluted with water. The suspension was filtered and the filter cake was washed with water and dried. The crude product was recrystallised from acetonitrile to afford (E)-2-[[3-(3-methoxy-4-((1-(2-oxo-2-(phenylamino)ethyl)-1H-1,2,3-triazol-4-yl)methoxy)phenyl)-1-oxo-2-propenyl]amino]benzoic acid (0.60 g, 80%) as a colourless solid; mp 220-222° C.; δH (400 MHz, DMSO-d6) 3.82 (s, 3H, OCH3), 5.21 (s, 2H, CH2), 5.36 (s, 2H, CH2), 6.80 (d, J=15.6 Hz, 1H, CH═CHCO), 7.08 (t, J=8.0 Hz, 1H, H4″), 7.16 (t, J3,4=J4,5=8.0 Hz, 1H, H4), 7.21-7.28 (m, 2H, H6′, H5′), 7.39 (s, 1H, H2′), 7.31 (t, J2″,3″=J3″,4″=J4″,5″=J5″,6″=8.0 Hz, 2H, H3″, H5″), 7.56-7.63 (m, 4H, CH═CHCO, H5, H2″, H6″), 8.00 (d, J3,4=8.0 Hz, 1H, H3), 8.27 (s, 1H, C═CHN), 8.62 (d, J5,6=8.0 Hz, 1H, H6), 10.48 (s, 1H, NH), 11.30 (s, 1H, NH), 13.60 (br s, 1H, CO2H); δC (100 MHz, DMSO-d6) 52.2, 55.6, 61.4, 110.5, 112.9, 116.6, 119.2, 120.1, 120.4, 122.6, 122.8, 123.8, 126.6, 127.6, 129.0, 131.2, 134.1, 138.5, 141.1, 141.7, 142.2, 149.1, 149.4, 164.2, 169.5; HRMS (ESI) calculated for C28H25N5O6 [M+Na]+ 550.1697. found 550.1691; vmax 1239, 1585, 1665, 2605, 3000, 3250 cm−1.

Workup

  1. filtrationThe suspension was filtered
  2. washthe filter cake was washed with water
  3. customdried
  4. customThe crude product was recrystallised from acetonitrile

Sources & evidence

ORD record
ord-5a3f67c1b2b34dd9863e3c7bd815ab27
Source dataset
uspto-grants-2014_07
Patent number
US08765812B2

Reaction notes

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