Triethylamine → HCID 66616147, compound

HRID 2367062Notes

Reaction equation

HRID 2367062 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[C:9]([CH3:14])([CH3:13])[C:10]([OH:12])=O.ClC(Cl)(OC(=O)OC(Cl)(Cl)Cl)Cl.C(N(CC)CC)C.[CH2:34]([N:41]1[CH2:46][CH2:45][CH:44]([NH2:47])[CH2:43][CH2:42]1)[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1>O1CCCC1>[CH2:34]([N:41]1[CH2:46][CH2:45][CH:44]([NH:47][C:10](=[O:12])[C:9]([C:3]2[CH:4]=[C:5]([F:8])[CH:6]=[CH:7][C:2]=2[Br:1])([CH3:14])[CH3:13])[CH2:43][CH2:42]1)[C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1

Participants

6

Reactant 4

HCID 8471Triethylamine2×HCID 94429TriphosgeneHCID 4158521-Benzyl-4-piperidylamineHCID 66616023HCID 66616023, compound

Product 1

HCID 66616147HCID 66616147, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 2-(2-bromo-5-fluorophenyl)-2-methylpropanoic acid (510 mg, 1.95 mmol, EXAMPLE 44, Step 1) in tetrahydrofuran (20 mL) were added triphosgene (197 mg, 0.66 mmol) and triethylamine (0.288 mL, 2.05 mmol). The mixture was stirred at room temperature for 30 min and was filtered. The filtrate was added drop-wise into a solution of 1-benzyl-4-aminopiperidine (372 mg, 1.95 mmol) and triethylamine (0.288 mL, 2.05 mmol) in tetrahydrofuran (20 mL). The mixture was stirred at room temperature for overnight.

Workup

  1. filtrationwas filtered
  2. stirringThe mixture was stirred at room temperature for overnight

Sources & evidence

ORD record
ord-0ccee0e05066462f84d6625587bfaa68
Source dataset
uspto-grants-2014_04
Patent number
US08697877B2

Reaction notes

Loading…