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Triethylamine → HCID 178425366, compound

HRID 642829
Notes
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Reaction equation

HRID 642829 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:30](O)=[O:31])[CH2:19][C:20]3[CH:28]=[C:27]([CH3:29])[C:23]4[NH:24][CH:25]=[N:26][C:22]=4[CH:21]=3)=[O:16])[CH2:11][CH2:10]2)[CH2:7][CH2:6][C:5]2[CH:33]=[CH:34][CH:35]=[CH:36][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.[CH3:66][S:67]([N:70]1[CH2:75][CH2:74][CH:73]([CH:76]2[CH2:81][CH2:80][NH:79][CH2:78][CH2:77]2)[CH2:72][CH2:71]1)(=[O:69])=[O:68]>CN(C=O)C>[O:1]=[C:2]1[N:8]([CH:9]2[CH2:10][CH2:11][N:12]([C:15]([O:17][C@H:18]([CH2:19][C:20]3[CH:28]=[C:27]([CH3:29])[C:23]4[NH:24][CH:25]=[N:26][C:22]=4[CH:21]=3)[C:30]([N:79]3[CH2:78][CH2:77][CH:76]([CH:73]4[CH2:72][CH2:71][N:70]([S:67]([CH3:66])(=[O:69])=[O:68])[CH2:75][CH2:74]4)[CH2:81][CH2:80]3)=[O:31])=[O:16])[CH2:13][CH2:14]2)[CH2:7][CH2:6][C:5]2[CH:33]=[CH:34][CH:35]=[CH:36][C:4]=2[NH:3]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 47782601-(Methylsulfonyl)-4,4'-bipiperidineHCID 178425374(R)-1-carboxy-2-(7-methyl-1H-benzimidazol-5-yl)-ethyl 4-(2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidine-1-carboxylate

Product 1

HCID 178425366
HCID 178425366, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 120 mg (0.22 mmol) (R)-1-carboxy-2-(7-methyl-1H-benzimidazol-5-yl)-ethyl 4-(2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidine-1-carboxylate, 80 mg (0.25 mmol) TBTU, 40 μL (0.29 mmol) triethylamine and 80 mg (0.33 mmol) 1-methanesulphonyl-[4,4′]bipiperidinyl in 1.5 mL DMF was stirred overnight at RT. The reaction mixture was purified by HPLC without working up. The fractions containing the product were combined and lyophilised.

Workup

  1. customThe reaction mixture was purified by HPLC
  2. additionThe fractions containing the product

Sources & evidence

ORD record
ord-b227d082a33b42f28fe2540a0eebd8dd
Source dataset
uspto-grants-2010_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07696195B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes