Dimethyl Sulfoxide → HCID 54325653, compound

HRID 1264251Notes

Reaction equation

Cl[C:2]1[N:7]=[C:6]([C:8]2[CH:16]=[CH:15][C:11]([C:12]([OH:14])=[O:13])=[CH:10][CH:9]=2)[CH:5]=[CH:4][N:3]=1.[CH3:17]S(C)=O.[N:21]1(CCN)[CH2:26][CH2:25][O:24][CH2:23][CH2:22]1.C[N:31]([CH:33]=O)C>>[N:21]1([N:31]([CH2:33][CH3:17])[C:2]2[N:7]=[C:6]([C:8]3[CH:16]=[CH:15][C:11]([C:12]([OH:14])=[O:13])=[CH:10][CH:9]=3)[CH:5]=[CH:4][N:3]=2)[CH2:22][CH2:23][O:24][CH2:25][CH2:26]1

Participants

Reactant 4

HCID 679Dimethyl Sulfoxide

HCID 6228Dimethylformamide

HCID 4082852-Morpholinoethylamine

HCID 186174554-(2-Chloro-4-pyrimidinyl)benzoic acid

Product 1

HCID 54325653HCID 54325653, compound

Conditions

Temperature: 80 °C

Procedure

To a solution of 4-[2-chloro-pyrimidin-4-yl]-benzoic acid (234 mg, 1 mmol, reference example 11g) in DMF (or DMSO) (3 mL) is added 2-(morpholin-4-yl)-ethyl amine (275 μL, 2.1 mmol). The resulting mixture was warmed to 80° C. and stirred for 4 h. The reaction mixture was then concentrated under a stream of nitrogen and the residue purified by reverse phase HPLC to give 166 mg of the title compound. 1H NMR (DMSO-d6) ? 3.18 (m, 2H), 3.40 (m, 2H), 3.50-3.80 (m, 6H), 3.97 (m, 2H) 7.33 (d, J=5 Hz, 1H), 7.53 (bt, 1H), 8.07 (d, J=8 Hz, 2H), 8.25 (d, J=8 Hz, 2H), 8.49 (d, J=5 Hz, 1H), 9.70 (bs, 1H). MS (ion spray) m/z 329 (M+H)+.

Workup

concentrationThe reaction mixture was then concentrated under a stream of nitrogen
customthe residue purified by reverse phase HPLC

Sources & evidence

ORD record: ord-b1d89893714847c58ef32cec9a67a6b4
Source dataset: uspto-grants-2003_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06541505B1

Reaction notes

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