2-Thiopheneacetic acid → HCID 86714427, compound

HRID 1750218Notes

Reaction equation

[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][C:7]([OH:9])=O.C1C=NC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.[CH3:29][O:30][C:31](=[O:47])[C:32]1[CH:37]=[CH:36][C:35]([NH:38][CH2:39][CH:40]2[CH2:45][CH2:44][CH2:43][CH2:42][CH2:41]2)=[C:34]([NH2:46])[CH:33]=1>CN(C=O)C.O.C(Cl)CCl>[CH3:29][O:30][C:31](=[O:47])[C:32]1[CH:37]=[CH:36][C:35]([NH:38][CH2:39][CH:40]2[CH2:41][CH2:42][CH2:43][CH2:44][CH2:45]2)=[C:34]([NH:46][C:7](=[O:9])[CH2:6][C:2]2[S:1][CH:5]=[CH:4][CH:3]=2)[CH:33]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 8.94 g of thiophen-2-yl-acetic acid in 130 ml of dry DMF 8.56 g of HOAT, 12.06 g of EDC and 30 ml of DIPEA were added at 0° C. After 30 min 15.00 g of 3-Amino-4-(cyclohexylmethyl-amino)-benzoic acid methyl ester were added and the reaction was stirred at 80° C. for 48 h. The reaction was then poured into water and extracted with ethyl acetate three times. The combined organic phases were washed with saturated aqueous sodium bicarbonate solution and brine, dried over magnesium sulphate and concentrated. The crude product was purified by chromatography (silica, ethyl acetate/heptane) to yield 22.00 g (100%) of 4-(Cyclohexylmethyl-amino)-3-(2-thiophen-2-yl-acetylamino)-benzoic acid methyl ester.

Workup

extractionextracted with ethyl acetate three times
washThe combined organic phases were washed with saturated aqueous sodium bicarbonate solution and brine
dry with materialdried over magnesium sulphate
concentrationconcentrated
customThe crude product was purified by chromatography (silica, ethyl acetate/heptane)

Sources & evidence

ORD record: ord-f911682c6345411c8ca1376fc8484d6b
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09156796B2

Reaction notes

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