Triethylamine → HCID 57387175, compound

HRID 406997Notes

Reaction equation

HRID 406997 reaction equation
Cl.[NH:2]1[CH2:7][CH2:6][CH:5]([N:8]2[CH:12]=[C:11]([C:13]3[CH:36]=[CH:35][C:16]4[N:17]([C:20]5[CH:21]=[C:22]([NH:26][C:27]([NH:29][CH2:30][C:31]([F:34])([F:33])[F:32])=[O:28])[CH:23]=[CH:24][CH:25]=5)[CH:18]=[N:19][C:15]=4[CH:14]=3)[CH:10]=[N:9]2)[CH2:4][CH2:3]1.ClC(OC1C=CC([N+]([O-])=O)=CC=1)=[O:39].[CH2:50]([N:52]([CH2:55]C)[CH2:53][CH3:54])[CH3:51].N1CCCC1>O1CCCC1>[N:52]1([C:55]([N:2]2[CH2:3][CH2:4][CH:5]([N:8]3[CH:12]=[C:11]([C:13]4[CH:36]=[CH:35][C:16]5[N:17]([C:20]6[CH:21]=[C:22]([NH:26][C:27]([NH:29][CH2:30][C:31]([F:33])([F:32])[F:34])=[O:28])[CH:23]=[CH:24][CH:25]=6)[CH:18]=[N:19][C:15]=5[CH:14]=4)[CH:10]=[N:9]3)[CH2:6][CH2:7]2)=[O:39])[CH2:53][CH2:54][CH2:51][CH2:50]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 31268PyrrolidineHCID 821294-Nitrophenyl chloroformateHCID 67980207N-{3-[5-(1-piperidin-4-yl-1H-pyrazol-4-yl)-1H-benzimidazol-1-yl]phenyl}-N'-(2,2,2-trifluoroethyl)urea HCl salt

Product 1

HCID 57387175HCID 57387175, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-{3-[5-(1-piperidin-4-yl-1H-pyrazol-4-yl)-1H-benzimidazol-1-yl]phenyl}-N′-(2,2,2-trifluoroethyl)urea HCl salt (20.0 mg, 0.0385 mmol) in tetrahydrofuran (1 mL) was added p-nitrophenyl chloroformate (12 mg, 0.058 mmol), triethylamine (16 μL, 0.12 mmol). The solution was stirred at r.t. for 1 h, then pyrrolidine (6.4 μL, 0.077 mmol) was added. The reaction solution was stirred at r.t. overnight, and then heated at 100° C. 2 h. LC/MS analysis showed reaction was finished. The reaction solution was concentrated under reduced pressure to dryness. The residue was dissolved in MeOH, and purified by RP-HPLC (pH=10) to afford the desired compound. LCMS (M+H)+: m/z=581.3

Workup

  1. stirringThe reaction solution was stirred at r.t. overnight
  2. temperatureheated at 100° C
  3. custom2 h
  4. customreaction
  5. concentrationThe reaction solution was concentrated under reduced pressure to dryness
  6. dissolutionThe residue was dissolved in MeOH
  7. custompurified by RP-HPLC (pH=10)

Sources & evidence

ORD record
ord-926e3b4679284e108ddde876c508aad6
Source dataset
uspto-grants-2014_06
Patent number
US08754114B2

Reaction notes

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