Dimethylamine → HCID 178425802, compound

HRID 1487871Notes

Reaction equation

HRID 1487871 reaction equation
Cl[CH2:2][CH2:3][C:4]1[NH:5][C:6]([C:10]2[CH:11]=[C:12]([CH:29]=[CH:30][C:31]=2[CH3:32])[C:13]([N:15]2[CH2:20][CH2:19][CH:18]([C:21]3[CH:28]=[CH:27][C:24]([C:25]#[N:26])=[CH:23][CH:22]=3)[CH2:17][CH2:16]2)=[O:14])=[C:7]([CH3:9])[N:8]=1.[CH3:33][NH:34][CH3:35]>CCO>[CH3:33][N:34]([CH3:35])[CH2:2][CH2:3][C:4]1[NH:5][C:6]([C:10]2[CH:11]=[C:12]([CH:29]=[CH:30][C:31]=2[CH3:32])[C:13]([N:15]2[CH2:20][CH2:19][CH:18]([C:21]3[CH:28]=[CH:27][C:24]([C:25]#[N:26])=[CH:23][CH:22]=3)[CH2:17][CH2:16]2)=[O:14])=[C:7]([CH3:9])[N:8]=1

Participants

4

Reactant 2

HCID 674DimethylamineHCID 1784258004-(1-(3-(2-(2-Chloroethyl)-4-methyl-1H-imidazol-5-yl)-4-methylbenzoyl)piperidin-4-yl)benzonitrile2×

Product 1

HCID 178425802HCID 178425802, compoundYield 24%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
100 °C

Procedure

Into a vessel with condensor, was placed a solution of 4-(1-(3-(2-(2-chloroethyl)-4-methyl-1H-imidazol-5-yl)-4-methylbenzoyl)piperidin-4-yl)benzonitrile (compound 24.1, 26 mg, 0.06 mmol, 1.00 equiv) in EtOH (10 mL). Dimethylamine (1 M in THF, 0.3 mL, 0.3 mmol) was added and the mixture was sealed under a nitrogen balloon. The resulting solution was stirred overnight with a 100° C. oil bath. After cooling to room temperature, the resulting mixture was concentrated under reduced pressure and the crude product was purified by Prep-HPLC with the following conditions (1#-Pre-HPLC-001(SHIMADZU)): Column,) (Bridge Shield RP18 OBD Column, 5 um, 19*150 mm; mobile phase, WATER WITH 0.03% NH3H2O and CH3CN (31% CH3CN up to 43% in 7 min, up to 100% in 0.5 min, down to 31% in 3.5 min); Detector, Waters 2489, 254 & 220 nm. The fractions containing pure compound were combined and lyophilized to yield 6.3 mg (24%) of the title compound as a white solid. m/z (ES+) 456 (M+H)+.

Workup

  1. customInto a vessel with condensor, was placed
  2. customthe mixture was sealed under a nitrogen balloon
  3. temperatureAfter cooling to room temperature
  4. concentrationthe resulting mixture was concentrated under reduced pressure
  5. customthe crude product was purified by Prep-HPLC with the following conditions (1#-Pre-HPLC-001(SHIMADZU))
  6. waitmobile phase, WATER WITH 0.03% NH3H2O and CH3CN (31% CH3CN up to 43% in 7 min
  7. waitup to 100% in 0.5 min
  8. waitdown to 31% in 3.5 min)
  9. additionThe fractions containing pure compound

Sources & evidence

ORD record
ord-befb3ca5fbb943d0a8c17e82564fd0a8
Source dataset
uspto-grants-2016_08
Patent number
US09428502B2

Reaction notes

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