Triethylamine → HCID 57529907, compound

HRID 643620Notes

Reaction equation

HRID 643620 reaction equation
[O:1]=[C:2]1[N:8]([CH:9]2[CH2:14][CH2:13][N:12]([C:15]([O:17][C@@H:18]([C:28]([OH:30])=O)[CH2:19][C:20]3[CH:25]=[CH:24][C:23]([CH3:26])=[C:22]([Cl:27])[CH:21]=3)=[O:16])[CH2:11][CH2:10]2)[CH2:7][CH2:6][C:5]2[CH:31]=[CH:32][CH:33]=[CH:34][C:4]=2[NH:3]1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C(N(CC)CC)C.[CH3:64][N:65]1[CH2:70][CH2:69][N:68]([CH:71]2[CH2:76][CH2:75][NH:74][CH2:73][CH2:72]2)[CH2:67][CH2:66]1.C([O-])(O)=O.[Na+]>C1COCC1>[O:1]=[C:2]1[N:8]([CH:9]2[CH2:14][CH2:13][N:12]([C:15]([O:17][C@H:18]([CH2:19][C:20]3[CH:25]=[CH:24][C:23]([CH3:26])=[C:22]([Cl:27])[CH:21]=3)[C:28]([N:74]3[CH2:73][CH2:72][CH:71]([N:68]4[CH2:67][CH2:66][N:65]([CH3:64])[CH2:70][CH2:69]4)[CH2:76][CH2:75]3)=[O:30])=[O:16])[CH2:11][CH2:10]2)[CH2:7][CH2:6][C:5]2[CH:31]=[CH:32][CH:33]=[CH:34][C:4]=2[NH:3]1

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 7957071-Methyl-4-(piperidin-4-yl)piperazineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 67301664HCID 67301664, compound

Product 1

HCID 57529907HCID 57529907, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 100 mg (0.21 mmol) of (R)-1-carboxy-2-(3-chloro-4-methyl-phenyl)-ethyl 4-(2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidine-1-carboxylate, 70.0 mg (0.22 mmol) TBTU and 35 μL (0.27 mmol) triethylamine in 10 mL THF was stirred for 1 h at RT. Then 40 mg (0.22 mmol) 1-methyl-4-piperidin-4-yl-piperazine were added and the reaction mixture was then stirred overnight at RT. The reaction solution was stirred with 20 mL semisaturated NaHCO3 solution, extracted twice with 20 mL EtOAc and the combined organic phases were dried over Na2SO4. After the desiccant and solvent had been eliminated the residue was purified by chromatography (Alox, activity stage II-III DCM/MeOH 40:1).

Workup

  1. stirringThe reaction solution was stirred with 20 mL
  2. extractionextracted twice with 20 mL EtOAc
  3. dry with materialthe combined organic phases were dried over Na2SO4
  4. customwas purified by chromatography (Alox, activity stage II-III DCM/MeOH 40:1)

Sources & evidence

ORD record
ord-32dd73fe5b7d40d5ad1228dfe049f736
Source dataset
uspto-grants-2010_04
Patent number
US07700598B2

Reaction notes

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