Ethanol → HCID 58980794, compound

HRID 1181358Notes

Reaction equation

HRID 1181358 reaction equation
[NH2:1][C:2]1[CH:6]=[C:5]([C:7]2[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][CH:8]=2)[S:4][C:3]=1[C:14]([O:16]C)=O.[F:18][C:19]1([F:36])[CH2:23][CH2:22][N:21]([CH2:24][CH2:25][O:26][C:27]2[CH:33]=[CH:32][C:30]([NH2:31])=[CH:29][C:28]=2[O:34][CH3:35])[CH2:20]1.[CH2:37](O)C>>[Cl:13][C:10]1[CH:9]=[CH:8][C:7]([C:5]2[S:4][C:3]3[C:14](=[O:16])[N:31]([C:30]4[CH:32]=[CH:33][C:27]([O:26][CH2:25][CH2:24][N:21]5[CH2:22][CH2:23][C:19]([F:18])([F:36])[CH2:20]5)=[C:28]([O:34][CH3:35])[CH:29]=4)[CH:37]=[N:1][C:2]=3[CH:6]=2)=[CH:12][CH:11]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 2777492Methyl 3-amino-5-(4-chlorophenyl)thiophene-2-carboxylateHCID 58980809HCID 58980809, compound

Product 1

HCID 58980794HCID 58980794, compoundYield 22%

Conditions

Temperature
110 °C

Procedure

Methyl 3-amino-5-(4-chlorophenyl)thiophene-2-carboxylate (0.1367 g, 0.5107 mmol) was taken up in dimethylformamdide dimethyl acetal (3 mL) and heated to 110° C. The reaction was stirred for 3 h and then concentrated. 4-[2-(3,3-Difluoropyrrolidin-1-yl)ethoxy]-3-methoxyaniline (0.1389 g, 0.5107 mmol) in absolute ethanol (3 mL) was added to the residue and concentrated. Fresh absolute ethanol (1 mL) was added and the reaction heated to reflux. The reaction was stirred for 18 h and then cooled to RT and the precipitate was collected to give 0.058 g (0.1120 mmol, 22%) of the product as a white solid. 1H NMR (D6-DMSO) δ 8.38 (s, 1H), 7.96 (s, 1H, 7.91 (d, 2H, J=8.4 Hz), 7.56 (d, 2H, J=8.4 Hz), 7.18 (s, 1H), 7.11 (d, 1H, J=8.5 Hz), 7.04 (d, 1H, J=8.6 Hz), 4.12 (t, 2H, J=5.5 Hz), 3.77 (s, 3H), 3.00 (t, 2H, J=13.6 Hz), 2.85 (t, 2H, J=5.5 Hz), 2.81 (t, 2H, J=7.0 Hz), 2.22 (m, 2H). LRMS M+H

Workup

  1. concentrationconcentrated
  2. concentrationconcentrated
  3. additionFresh absolute ethanol (1 mL) was added
  4. temperaturethe reaction heated to reflux
  5. stirringThe reaction was stirred for 18 h
  6. temperaturecooled to RT
  7. customthe precipitate was collected

Sources & evidence

ORD record
ord-74bdd90efa794466941a4ce6f3c5a473
Source dataset
uspto-grants-2007_10
Patent number
US07285557B2

Reaction notes

Loading…