Triethylamine → 4'-(Cyclopropylcarbamoyl)biphenyl-4-yl N-methyl-N-(3-(pyridin-4-yl)benzyl)carbamate

HRID 2205300Notes

Reaction equation

HRID 2205300 reaction equation
[C:1](=O)([O:21]N1C(=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:20])[NH:16][CH:17]3[CH2:19][CH2:18]3)=[CH:11][CH:10]=2)=[CH:5][CH:4]=1.[CH3:30][NH:31][CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[C:35]([C:39]2[CH:44]=[CH:43][N:42]=[CH:41][CH:40]=2)[CH:34]=1.C(N(CC)CC)C>ClCCl>[CH3:30][N:31]([CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[C:35]([C:39]2[CH:40]=[CH:41][N:42]=[CH:43][CH:44]=2)[CH:34]=1)[C:1](=[O:21])[O:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[CH:14]=[CH:13][C:12]([C:15](=[O:20])[NH:16][CH:17]3[CH2:19][CH2:18]3)=[CH:11][CH:10]=2)=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 7060574N-methyl(3-(pyridin-4-yl)phenyl)methanamineHCID 867220724-[4-(Cyclopropylcarbamoyl)phenyl]phenyl 2,5-dioxopyrrolidin-1-yl carbonate

Product 1

HCID 714929724'-(Cyclopropylcarbamoyl)biphenyl-4-yl N-methyl-N-(3-(pyridin-4-yl)benzyl)carbamate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Into a 100-mL round-bottom flask was placed a solution of 4-[4-(cyclopropylcarbamoyl)phenyl]phenyl 2,5-dioxopyrrolidin-1-yl carbonate (600 mg, 1.52 mmol, 1.00 equiv) in dichloromethane (40 mL), N-methyl([[3-(pyridin-4-yl)phenyl]methyl])amine (301 mg, 1.52 mmol, 1.00 equiv) and triethylamine (153 mg, 1.51 mmol, 0.99 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-80ae7334799b4a40a0485554ca6c3d1e
Source dataset
uspto-grants-2016_06
Patent number
US09371285B2

Reaction notes

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