Triethylamine → HCID 86670934, compound

HRID 515276Notes

Reaction equation

HRID 515276 reaction equation
[NH2:1][C:2]1[CH:31]=[CH:30][C:5]([O:6][CH:7]2[CH2:12][CH2:11][N:10]([CH2:13][C:14]3[CH:19]=[CH:18][C:17]([C:20]([OH:29])([C:25]([F:28])([F:27])[F:26])[C:21]([F:24])([F:23])[F:22])=[CH:16][CH:15]=3)[CH2:9][CH2:8]2)=[C:4]([Br:32])[CH:3]=1.Cl[C:34](OC1C=CC([N+]([O-])=O)=CC=1)=[O:35].[O:46]1[CH2:51][CH2:50][CH:49]([NH2:52])[CH2:48][CH2:47]1.C(N(CC)CC)C>O1CCCC1>[Br:32][C:4]1[CH:3]=[C:2]([NH:1][C:34]([NH:52][CH:49]2[CH2:50][CH2:51][O:46][CH2:47][CH2:48]2)=[O:35])[CH:31]=[CH:30][C:5]=1[O:6][CH:7]1[CH2:12][CH2:11][N:10]([CH2:13][C:14]2[CH:15]=[CH:16][C:17]([C:20]([OH:29])([C:25]([F:28])([F:26])[F:27])[C:21]([F:22])([F:23])[F:24])=[CH:18][CH:19]=2)[CH2:9][CH2:8]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 821294-Nitrophenyl chloroformateHCID 4192234-AminotetrahydropyranHCID 866709332-(4-((4-(4-Amino-2-bromophenoxy)piperidin-1-yl)methyl)phenyl)-1,1,1,3,3,3-hexafluoropropan-2-ol

Product 1

HCID 86670934HCID 86670934, compoundYield 43.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-(4-((4-(4-Amino-2-bromophenoxy)piperidin-1-yl)methyl)phenyl)-1,1,1,3,3,3-hexafluoropropan-2-ol (0.379 mmol, 200 mg) and 4-nitrophenyl chloroformate (0.379 mmol, 76 mg) were combined in tetrahydrofuran (1 mL) and the mixture stirred at room temperature for 45 minutes. Tetrahydro-2H-pyran-4-amine (0.379 mmol, 38.4 mg) followed by triethylamine (1.138 mmol, 115 mg) were added and the mixture stirred overnight. The mixture was concentrated under reduced pressure and the resulting residue was purified by HPLC then treated with strong cation exchange column chromatography to afford the title compound (107 mg).

Workup

  1. additionwere added
  2. stirringthe mixture stirred overnight
  3. concentrationThe mixture was concentrated under reduced pressure
  4. customthe resulting residue was purified by HPLC
  5. additionthen treated with strong cation exchange column chromatography

Sources & evidence

ORD record
ord-101b4942c8c4439ba432b43dd174ad52
Source dataset
uspto-grants-2015_08
Patent number
US09108939B2

Reaction notes

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