Triphenylphosphine → 3-[Isopropyl-(3-methyl-cyclopent-3-enecarbonyl)-amino]-5-phenyl-thiophene-2-carboxylic acid methyl ester

HRID 1015648Notes

Reaction equation

HRID 1015648 reaction equation
[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:8][C:9]=1[NH:10][CH:11]([CH3:13])[CH3:12])=[O:4].[CH3:20][C:21]1[CH2:22][CH:23]([C:26](O)=[O:27])[CH2:24][CH:25]=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C(=O)N(Cl)C(=O)C1>>[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)=[CH:8][C:9]=1[N:10]([CH:11]([CH3:13])[CH3:12])[C:26]([CH:23]1[CH2:24][CH:25]=[C:21]([CH3:20])[CH2:22]1)=[O:27])=[O:4]

Participants

5

Reactant 4

HCID 11776TriphenylphosphineHCID 31398ChlorosuccinimideHCID 11737447Methyl 3-(isopropyl-amino)-5-phenylthiophene-2-carboxylateHCID 125754193-Methyl-cyclopent-3-enecarboxylic acid

Product 1

HCID 672993023-[Isopropyl-(3-methyl-cyclopent-3-enecarbonyl)-amino]-5-phenyl-thiophene-2-carboxylic acid methyl esterYield 61%

Procedure

The coupling of the 3-Isopropylamino-5-phenyl-thiophene-2-carboxylic acid methyl ester (82 mg, 0.3 mmol) and the 3-Methyl-cyclopent-3-enecarboxylic acid (45 mg, 0.357 mmol) using PPh3 (95.4 mg, 0.363 mmol) and NCS (48.5 mg, 0.363 mmol) furnished the 3-[Isopropyl-(3-methyl-cyclopent-3-enecarbonyl)-amino]-5-phenyl-thiophene-2-carboxylic acid methyl ester (70 mg, 61% yield) 1H NMR (CDCl3, 400 MHz 1:1 mixture of, rotamers), 7.68-7.64 (m, 4H), 7.5-7.4 (m, 6H), 7.1 (s, 1H), 7.09 (s, 1H), 5.2 (s, 1H), 5.1 (s, 1H), 5.06-4.98 (m, 2H), 3.88 (s, 3H), 3.87 (s, 3H), 3.08-3.0 (m, 2H), 2.85-2.76 (m, 2H), 2.5-2.42 (m, 2H), 2.3-2.1 (m, 4H), 1.69 (s, 3H), 1.64 (s, 3H), 1.24 (d, J=6.7 Hz, 3H), 1.23 (d, J=6.7 Hz, 3H), 1.01 (d, J=6.9 Hz, 3H), 1.007 (d, J=6.8 Hz, 3H).

Sources & evidence

ORD record
ord-434dae46874f4623877a808c8349005a
Source dataset
uspto-grants-2011_07
Patent number
US07985769B2

Reaction notes

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