Triethylamine → HCID 66779288, compound

HRID 1470389Notes

Reaction equation

[O:1]([C:8]1[CH:30]=[CH:29][C:11]([O:12][C:13]2[CH:18]=[CH:17][N:16]=[C:15]3[CH:19]=[C:20]([C:22]4[CH:23]=[C:24]([CH:26]=[CH:27][CH:28]=4)[NH2:25])[O:21][C:14]=23)=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:38](Cl)(=[O:41])[CH:39]=[CH2:40]>CN1CCCC1=O.C(Cl)Cl>[O:1]([C:8]1[CH:30]=[CH:29][C:11]([O:12][C:13]2[CH:18]=[CH:17][N:16]=[C:15]3[CH:19]=[C:20]([C:22]4[CH:23]=[C:24]([NH:25][C:38](=[O:41])[CH:39]=[CH2:40])[CH:26]=[CH:27][CH:28]=4)[O:21][C:14]=23)=[CH:10][CH:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a 20-mL glass vial was added 3-[7-(4-phenoxyphenoxy)furo[3,2-b]pyridin-2-yl]aniline (30.00 mg; 0.08 mmol), N,N-diethylethanamine (0.02 ml; 0.15 mmol) suspended in 1-methylpyrrolidin-2-one (0.35 ml) and DCM (2.00 ml). The resulting mixture was cooled to 0° C. and stirred for 5 minutes. Acryloyl chloride (0.02 ml; 0.23 mmol) was added. The ice bath was left to melt. The reaction mixture was then stirred at room temperature overnight. The mixture was concentrated. The crude mixture was purified using Biotage column chromatography (0-40% MeOH/EtOAc) to afford the title compound as a white solid (5.00 mg, 15%). HPLC (method F): 100%, RT=4.538 min. 1H NMR (DMSO-d6) δ [ppm] 10.29 (s, 1H), 8.31 (d, 1H), 8.22 (s, 1H), 7.74 (d, 1H), 7.63 (d, 1H), 7.55 (s, 1H), 7.43 (t, 1H), 7.35 (t, 2H), 7.31 (d, 2H), 7.09 (d, 3H), 7.02 (d, 2H), 6.66 (d, 1H), 6.41-6.36 (dd, 1H), 6.25 (d, 1H), 5.73 (d, 1H). MS: m/z=449 [M+H]+, RT=4.08 min.

Workup

stirringThe reaction mixture was then stirred at room temperature overnight
concentrationThe mixture was concentrated
customThe crude mixture was purified

Sources & evidence

ORD record: ord-49ad40e38a3f4b5599f1b94635ea4a17
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09006440B2

Reaction notes

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