Tetrahydrofuran → HCID 66928769, compound

HRID 1362985Notes

Reaction equation

[F:1][CH:2]1[CH2:7][CH2:6][N:5]([CH2:8][CH2:9][O:10][C:11]2[CH:16]=[CH:15][C:14]([NH2:17])=[CH:13][C:12]=2[C:18]2[N:19]([CH3:23])[N:20]=[CH:21][CH:22]=2)[CH2:4][CH2:3]1.[F:24][C:25]1C=CC(C(Cl)=O)=[CH:27][C:26]=1[Cl:34].C(N(CC)CC)C.[CH2:42]1[CH2:46][O:45][CH2:44][CH2:43]1>>[Cl:34][C:26]1[C:25]([F:24])=[C:42]([CH:43]=[CH:44][CH:27]=1)[C:46]([NH:17][C:14]1[CH:15]=[CH:16][C:11]([O:10][CH2:9][CH2:8][N:5]2[CH2:6][CH2:7][CH:2]([F:1])[CH2:3][CH2:4]2)=[C:12]([C:18]2[N:19]([CH3:23])[N:20]=[CH:21][CH:22]=2)[CH:13]=1)=[O:45]

Participants

Reactant 4

HCID 8028Tetrahydrofuran

HCID 8471Triethylamine

HCID 27365483-Chloro-4-fluorobenzoyl Chloride

HCID 58964271HCID 58964271, compound

Product 1

HCID 66928769HCID 66928769, compoundYield 50%

Procedure

A mixture of 4-[2-(4-fluoro-piperidin-1-yl)-ethoxy]-3-(2-methyl-2H-pyrazol-3-yl)-phenylamine (80 mg, 0.25 mmol), 4-fluoro-3-chlorobenzoyl chloride (48 mg, 0.25 mmol), and triethylamine (0.3 mL) in THF (3 mL) was stirred at r.t. for 10 min. The solvent was concentrate in vacuo and the crude was purified by HPLC to give the title compound (58 mg, 50%) as a white solid as TFA salt. 1H NMR (acetone-d6, 400 MHz) δ 2.02-2.24 (m, 4H), 3.08-3.18 (m, 2H), 3.32-3.42 (m, 2H), 3.63 (t, J=4.55 Hz, 2H), 3.80 (s, 3H), 4.59 (t, J=4.55 Hz, 2H); 4.91-5.03 (m, 1H), 6.30 (d, J=1.77 Hz, 1H), 7.23 (d, J=8.84 Hz, 1H), 7.43-7.51 (m, 2H), 7.81 (t, J=2.27 Hz, 1H), 7.91-7.97 (m, 1H), 8.02-8.08 (n, 1H), 8.18 (dd, J=2.53, 7.33 Hz, 1H), 9.71 (s, 1H). Exact mass calculated for C24H25ClF2N4O2 503.1. found 504.1/506.1 (MH+).

Workup

concentrationThe solvent was concentrate in vacuo
customthe crude was purified by HPLC

Sources & evidence

ORD record: ord-ca21a271235240a9930f8d3f0af7c9d4
Source dataset: uspto-grants-2011_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07884101B2

Reaction notes

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