N-methyl-2-pyrrolidone → HCID 54577788, compound

HRID 1845908Notes

Reaction equation

HRID 1845908 reaction equation
[O:1]=[C:2]1[N:6]([CH2:7][CH:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)[C:5]2[CH:14]=[CH:15][C:16]([C:18]3[CH:25]=[CH:24][CH:23]=[CH:22][C:19]=3[C:20]#[N:21])=[CH:17][C:4]=2[S:3]1.Br[C:27]1[N:32]=[CH:31][CH:30]=[CH:29][N:28]=1.CN1C(=O)CCC1.CCN(C(C)C)C(C)C>CO>[O:1]=[C:2]1[N:6]([CH2:7][CH:8]2[CH2:9][CH2:10][N:11]([C:27]3[N:32]=[CH:31][CH:30]=[CH:29][N:28]=3)[CH2:12][CH2:13]2)[C:5]2[CH:14]=[CH:15][C:16]([C:18]3[CH:25]=[CH:24][CH:23]=[CH:22][C:19]=3[C:20]#[N:21])=[CH:17][C:4]=2[S:3]1

Participants

6

Reactant 4

HCID 13387N-methyl-2-pyrrolidoneHCID 783452-BromopyrimidineHCID 81531DiisopropylethylamineHCID 54577789HCID 54577789, compound

Product 1

HCID 54577788HCID 54577788, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
100 °C

Procedure

To a microwave vial was added 2-[2-oxo-3-(piperidin-4-ylmethyl)-2,3-dihydro-1,3-benzothiazol-6-yl]benzonitrile (11-3) (0.029 g, 0.075 mmol), 2-bromopyrimidine (0.0143 g, 0.090 mmol), NMP (0.7 mL), and DIPEA (0.033 mL, 0.188 mmol). The reaction mixture was then heated under microwave irradiation at 100° C. for 10 minutes. The crude reaction mixture was then allowed to cool to room temperature, diluted with methanol, filtered and concentrated. Purification of crude reaction mixture by reverse phase chromatography (Waters Sunfire MSC18, 10% acetonitrile/0.1% trifluoroacetic acid/water→100% acetonitrile/0.1% trifluoroacetic acid/water) gave 2-{2-oxo-3-[(1-pyrimidin-2-ylpiperidin-4-yl)methyl]-2,3-dihydro-1,3-benzothiazol-6-yl}benzonitrile (11-4) as a brown solid. HRMS (M+H)+: observed=428.1544, calculated=428.1540.

Workup

  1. customThe crude reaction mixture
  2. temperatureto cool to room temperature
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customPurification of crude
  6. customreaction mixture by reverse phase chromatography (Waters Sunfire MSC18, 10% acetonitrile/0.1% trifluoroacetic acid/water→100% acetonitrile/0.1% trifluoroacetic acid/water)

Sources & evidence

ORD record
ord-775b3124dbd44467aa503ef10b78b672
Source dataset
uspto-grants-2015_02
Patent number
US08952005B2

Reaction notes

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