1-Hydroxybenzotriazole → HCID 44218978, compound

HRID 1093571Notes

Reaction equation

HRID 1093571 reaction equation
[C:1]1([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:6]=[CH:5][C:4]([C:7]([NH:9][CH2:10][C:11]([OH:13])=O)=[O:8])=[CH:3][CH:2]=1.CCN(C(C)C)C(C)C.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl.[F:51][C:52]([F:67])([F:66])[C:53]1[CH:65]=[CH:64][CH:63]=[CH:62][C:54]=1[O:55][CH:56]1[CH2:61][CH2:60][NH:59][CH2:58][CH2:57]1>CN(C=O)C.O>[O:13]=[C:11]([N:59]1[CH2:58][CH2:57][CH:56]([O:55][C:54]2[CH:62]=[CH:63][CH:64]=[CH:65][C:53]=2[C:52]([F:51])([F:66])[F:67])[CH2:61][CH2:60]1)[CH2:10][NH:9][C:7]([C:4]1[CH:3]=[CH:2][C:1]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:6][CH:5]=1)=[O:8]

Participants

8

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 2629432-((4-Phenylphenyl)formamido)acetic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 50187904-[2-(Trifluoromethyl)phenoxy]piperidine

Product 1

HCID 44218978HCID 44218978, compoundYield 46%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of [(biphenyl-4-carbonyl)-amino]-acetic acid (0.09128 g, 0.00036 mol) in DMF (2 mL) was added DIPEA (0.126 g, 0.00098 mol), HOBt (0.05266 g, 0.0003901 mol) and EDCI.HCl (0.07457 g, 0.00039 mol) at ambient temperature. After 2 minutes 4-(2-trifluoromethyl-phenoxy)-piperidine trifluoroactetate (0.11 g, 0.00033 mol) was added and the resulting mixture was stirred at the same temperature overnight. The reaction mixture was diluted with cold water and the resulting precipitate was isolated by filtration and dried to afford 0.072 g (46%) of biphenyl-4-carboxylic acid {2-oxo-2-[4-(2-trifluoromethyl-phenoxy)-piperidin-1-yl]-ethyl}-amide. LCMS: 483.18 (M+1)+, 95.73%, 1H NMR (CDCl3): δ 7.9 (d, 2H), 7.64-7.54 (m, 4H), 7.46-7.3 (m, 4H), 7.02-6.9 (q, 2H), 4.75 (s, 1H), 4.4-4.2 (dd, 2H), 4.2-4.0 (m, 2H), 3.65-3.35 (m, 4H), 2.05-1.8 (m, 4H).

Workup

  1. addition(0.11 g, 0.00033 mol) was added
  2. customthe resulting precipitate was isolated by filtration
  3. customdried

Sources & evidence

ORD record
ord-4baa2633990441ba9683d1a08ccc5383
Source dataset
uspto-grants-2012_03
Patent number
US08129376B2

Reaction notes

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