Triethylamine → HCID 71492974, compound

HRID 2205299Notes

Reaction equation

HRID 2205299 reaction equation
[C:1](=[O:27])(ON1C(=O)CCC1=O)[O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][C:12]([C:15](=[O:18])[NH:16][CH3:17])=[CH:11][CH:10]=2)=[CH:5][CH:4]=1.[CH3:28][NH:29][CH2:30][C:31]1[CH:32]=[C:33]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[CH:34]=[CH:35][CH:36]=1.C(N(CC)CC)C>ClCCl>[CH3:28][N:29]([CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[C:33]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[CH:32]=1)[C:1](=[O:27])[O:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[CH:10]=[CH:11][C:12]([C:15](=[O:18])[NH:16][CH3:17])=[CH:13][CH:14]=2)=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 53846799N-Methyl[1,1′-biphenyl]-3-methanamineHCID 86722071HCID 86722071, compound

Product 1

HCID 71492974HCID 71492974, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Into a 100-mL round-bottom flask was placed a solution of 4-[4-(methylcarbamoyl)phenyl]phenyl 2,5-dioxopyrrolidin-1-yl carbonate from Example 1 Step 4 (560 mg, 1.5 mmol, 1 equiv) in dichloromethane (40 mL), N-methyl (3-biphenyl)methylamine (301 mg, 1.5 mmol, 1 equiv) and triethylamine (153 mg, 1.5 mmol, 1 equiv). The resulting solution was stirred overnight at room temperature. The reaction mixture was washed with 2×20 mL of water and dried over anhydrous sodium sulfate. The resulting mixture was concentrated under vacuum. The crude product (650 mg) was purified by Prep-HPLC with the following conditions (1#-Pre-HPLC-002(Agilent)): Column, SunFire Prep C18, 19*150 mm 5 um; mobile phase, water and acetonitrile (10.0% acetonitrile up to 80.0% in 10 min, up to 100.0% in 1 min, down to 10.0% in 2 min); Detector, uv 220 & 254 nm. The title compound was obtained as a white solid.

Workup

  1. customInto a 100-mL round-bottom flask was placed
  2. washThe reaction mixture was washed with 2×20 mL of water
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationThe resulting mixture was concentrated under vacuum
  5. customThe crude product (650 mg) was purified by Prep-HPLC with the following conditions (1#-Pre-HPLC-002(Agilent))
  6. waitmobile phase, water and acetonitrile (10.0% acetonitrile up to 80.0% in 10 min
  7. waitup to 100.0% in 1 min
  8. waitdown to 10.0% in 2 min)

Sources & evidence

ORD record
ord-eb72ec60d294466ba91284c7f45eca0a
Source dataset
uspto-grants-2016_06
Patent number
US09371285B2

Reaction notes

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