Triethylamine → HCID 22275271, compound

HRID 1063991Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]([CH:20]([C:22]2[CH:34]=[CH:33][CH:32]=[CH:31][C:23]=2[O:24][CH2:25][CH2:26][CH2:27][C:28](O)=[O:29])[CH3:21])[C:12]2[CH:17]=[C:16]([F:18])[CH:15]=[CH:14][C:13]=2[F:19])(=[O:10])=[O:9])=[CH:4][CH:3]=1.C1C=CC2N(O)N=[N:41][C:39]=2C=1.CCN=C=NCCCN(C)C.CCN(CC)CC.CN.Cl>C(Cl)Cl.C(OCC)(=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]([CH:20]([C:22]2[CH:34]=[CH:33][CH:32]=[CH:31][C:23]=2[O:24][CH2:25][CH2:26][CH2:27][C:28]([NH:41][CH3:39])=[O:29])[CH3:21])[C:12]2[CH:17]=[C:16]([F:18])[CH:15]=[CH:14][C:13]=2[F:19])(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 25 °C

Procedure

A mixture of acid 4-[2-(1-([(4-chlorophenyl)sulfonyl]-2,5-difluoroanilino}ethyl)phenoxy]butanoic acid (107 mg, 0.21 mmol), HOBT (31 mg, 0.23 mmol), EDCI (44 mg, 0.23 mmol), Et3N (88 μL, 0.63 mmol) and CH3NH2.HCl (16 mg, 0.23 mmol) in CH2Cl2 (1.0 mL) was stirred at 25° C. for 13 h. The mixture was diluted with ethyl acetate. The organic solution was washed with H2O and sat. NaCl solution then dried over MgSO4. Concentration and chromatography afforded the amide (107 mg, 97%) as colorless gum: Rf 0.32 (10:20, hexane-ethyl acetate); 1H NMR (CDCl3, 300 MHz) δ 7.64 (d, 2H, J=6.9 Hz), 7.42 (d, 2H, J=7.8 Hz), 7.18 (t, 1H, J=8.7 Hz), 6.36-6.91 (m, 7H), 6.26 (q, 1H, 1=6.9 Hz), 4.13 (m, 1H), 4.05 (m, 1H), 2.78 (m, 4H), 2.57 (m, 1H), 2.23 (m, 2H), 1.55 (br s, 3H); LCMS m/z 524 (M+H+, C25H25ClF2N2O4S requires 522.99).

Workup

washThe organic solution was washed with H2O and sat. NaCl solution
dry with materialthen dried over MgSO4
concentrationConcentration and chromatography

Sources & evidence

ORD record: ord-1f0b86dc67e0440b9424772dd145443a
Source dataset: uspto-grants-2005_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06967196B1

Reaction notes

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