Triethylamine → HCID 67274143, compound

HRID 599767Notes

Reaction equation

HRID 599767 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:36](O)=[O:37])[CH2:19][C:20]3[CH:25]=[C:24]([CH3:26])[C:23]([O:27][CH2:28][C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)=[C:22]([CH3:35])[CH:21]=3)=[O:16])[CH2:11][CH2:10]2)[CH2:7][CH2:6][C:5]2[CH:39]=[CH:40][CH:41]=[CH:42][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.[N:72]1([CH:78]2[CH2:83][CH2:82][N:81]([CH2:84][C:85]([O:87][CH2:88][CH3:89])=[O:86])[CH2:80][CH2:79]2)[CH2:77][CH2:76][NH:75][CH2:74][CH2:73]1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[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:21]=[C:22]([CH3:35])[C:23]([O:27][CH2:28][C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)=[C:24]([CH3:26])[CH:25]=3)[C:36]([N:75]3[CH2:76][CH2:77][N:72]([CH:78]4[CH2:83][CH2:82][N:81]([CH2:84][C:85]([O:87][CH2:88][CH3:89])=[O:86])[CH2:80][CH2:79]4)[CH2:73][CH2:74]3)=[O:37])=[O:16])[CH2:11][CH2:10]2)[CH2:7][CH2:6][C:5]2[CH:39]=[CH:40][CH:41]=[CH:42][C:4]=2[NH:3]1

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 11430Potassium CarbonateHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 25208036(R)-2-(4-benzyloxy-3,5-dimethyl-phenyl)-1-carboxy-ethyl 4-(2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidine-1-carboxylateHCID 54188692HCID 54188692, compound

Product 1

HCID 67274143HCID 67274143, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2.80 g (4.90 mmol) (R)-2-(4-benzyloxy-3,5-dimethyl-phenyl)-1-carboxy-ethyl 4-(2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidine-1-carboxylate (Example 1g), 1.80 g (5.61 mmol) TBTU and 3.10 mL (22.08 mmol) triethylamine in 30 mL DMF was stirred for 1 h at RT. Then 2.00 g (5.48 mmol) ethyl (4-piperazin-1-yl-piperidin-1-yl)-acetate were added. The reaction mixture was stirred for 1 h at RT, poured onto 150 mL 15% K2CO3 solution and extracted with 200 mL EtOAc. The organic phase was extracted with 150 mL of 10% citric acid solution, the aqueous phase was made alkaline with 15% K2CO3 solution and extracted with 200 mL EtOAc. The organic phase was concentrated by evaporation i.vac. and the residue was purified by chromatography (silica gel, EtOH).

Workup

  1. extractionextracted with 200 mL EtOAc
  2. extractionThe organic phase was extracted with 150 mL of 10% citric acid solution
  3. extractionextracted with 200 mL EtOAc
  4. concentrationThe organic phase was concentrated by evaporation i.vac
  5. customand the residue was purified by chromatography (silica gel, EtOH)

Sources & evidence

ORD record
ord-8fe1cc7a4a404a8eb5babb22b37465e8
Source dataset
uspto-grants-2011_03
Patent number
US07897603B2

Reaction notes

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