Triethylamine → HCID 10025686, compound

HRID 1916602Notes

Reaction equation

HRID 1916602 reaction equation
C(N(CC)CC)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.[N:30]1([CH:35]([CH3:39])[C:36]([OH:38])=O)[CH2:34][CH2:33][CH2:32][CH2:31]1.[Cl:40][C:41]1[CH:46]=[CH:45][C:44]([C:47]2[CH:48]=[CH:49][C:50]([C:53]#[C:54][C:55]3[CH:60]=[CH:59][C:58]([NH2:61])=[CH:57][CH:56]=3)=[N:51][CH:52]=2)=[CH:43][CH:42]=1>C1COCC1.C([O-])(O)=O.[Na+]>[Cl:40][C:41]1[CH:46]=[CH:45][C:44]([C:47]2[CH:48]=[CH:49][C:50]([C:53]#[C:54][C:55]3[CH:56]=[CH:57][C:58]([NH:61][C:36](=[O:38])[CH:35]([N:30]4[CH2:31][CH2:32][CH2:33][CH2:34]4)[CH3:39])=[CH:59][CH:60]=3)=[N:51][CH:52]=2)=[CH:43][CH:42]=1

Participants

7

Reactant 4

HCID 8471Triethylamine2×HCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate2×HCID 31571772-(Pyrrolidin-1-yl)propanoic acid2×HCID 67364245HCID 67364245, compound

Product 1

HCID 10025686HCID 10025686, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 516892Sodium BicarbonateSolvent

Procedure

0.18 mL (1.31 mmol) triethylamine and 269 mg (0.84 mmol) TBTU are added successively to a solution of 100 mg (0.70 mmol) 2-pyrrolidin-1-yl-propionic acid in 10 mL THF. The solution is stirred for 1 h at RT and then 200 mg (0.66 mmol) 4-[5-(4-chloro-phenyl)-pyridin-2-ylethynyl]-phenylamine are added. The reaction solution is stirred overnight at RT. The reaction is incomplete. Therefore 100 mg (0.70 mmol) 2-pyrrolidin-1-yl-propionic acid in 10 mL THF is added to the reaction mixture (activated for 1 h by stirring with 0.18 mL (1.31 mmol) triethylamine and 269 mg (0.84 mmol) TBTU). The reaction solution is stirred for a further 16 h and diluted with NaHCO3 solution. The aqueous phase is extracted with EtOAc and the organic phase is dried over MgSO4. The solvent is eliminated i.vac. and further purification is carried out by column chromatography on silica gel (EtOAc/MeOH/NH3 8:2:0.2).

Workup

  1. stirringThe reaction solution is stirred overnight at RT
  2. stirringThe reaction solution is stirred for a further 16 h
  3. extractionThe aqueous phase is extracted with EtOAc
  4. dry with materialthe organic phase is dried over MgSO4
  5. customand further purification

Sources & evidence

ORD record
ord-8b67ed82214a4cada22524ea0c1a8d74
Source dataset
uspto-grants-2013_12
Patent number
US08618132B2

Reaction notes

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