Triethylamine → HCID 86722073, compound

HRID 2205301Notes

Reaction equation

HRID 2205301 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[CH:8]=[C:9]([CH2:13][N:14]([CH:18]([CH3:20])C)[C:15](Cl)=[O:16])[CH:10]=[CH:11][CH:12]=2)=[CH:3][CH:2]=1.[OH:21][C:22]1[CH:27]=[CH:26][C:25]([C:28]2[CH:37]=[CH:36][C:31]([C:32]([NH:34][CH3:35])=[O:33])=[CH:30][CH:29]=2)=[CH:24][CH:23]=1.[CH2:38](N(CC)CC)C>ClCCl>[CH2:18]([N:14]([CH2:13][C:9]1[CH:10]=[CH:11][CH:12]=[C:7]([C:4]2[CH:3]=[CH:2][N:1]=[CH:6][CH:5]=2)[CH:8]=1)[C:15](=[O:16])[O:21][C:22]1[CH:23]=[CH:24][C:25]([C:28]2[CH:37]=[CH:36][C:31]([C:32](=[O:33])[NH:34][CH3:35])=[CH:30][CH:29]=2)=[CH:26][CH:27]=1)[CH2:20][CH3:38]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 18183833HCID 18183833, compoundHCID 86722074HCID 86722074, compound

Product 1

HCID 86722073HCID 86722073, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Into a 50-mL round-bottom flask was placed a solution of N-[3-(4-pyridinyl)phenylmethyl]N-isopropylcarbamoyl chloride (310 mg, 1.07 mmol, 1 equiv) in dichloromethane (15 mL), 4-(4-hydroxyphenyl)-N-methylbenzamide from Example 1 Step 3 (291 mg, 1.28 mmol, 1.2 equiv) and triethylamine (216 mg, 2.13 mmol, 2 equiv). The resulting solution was stirred overnight at room temperature. The reaction was then quenched by the addition of 10 mL of water. The resulting solution was extracted with 20 mL of dichloromethane. The organic layer was dried over anhydrous sodium sulfate and concentrated under vacuum. The crude product was purified by Prep-HPLC with the following conditions (1#-Pre-HPLC-002(Agilent)): Column, Xbridge Prep C18, 5 um, 19*150 mm; mobile phase, water and CH3CN (45.0% CH3CN up to 75.0% in 10 min, hold 100.0% in 1 min, hold 45.0% in 2 min); Detector, uv 220 & 254 nm. The title compound was obtained as a white solid.

Workup

  1. customInto a 50-mL round-bottom flask was placed
  2. customThe reaction was then quenched by the addition of 10 mL of water
  3. extractionThe resulting solution was extracted with 20 mL of dichloromethane
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. concentrationconcentrated under vacuum
  6. customThe crude product was purified by Prep-HPLC with the following conditions (1#-Pre-HPLC-002(Agilent))
  7. waitmobile phase, water and CH3CN (45.0% CH3CN up to 75.0% in 10 min
  8. customin 1 min
  9. customin 2 min

Sources & evidence

ORD record
ord-c90fbb9ec7e5494089648965e2bba365
Source dataset
uspto-grants-2016_06
Patent number
US09371285B2

Reaction notes

Loading…