Methylamine → HCID 59835763, compound

HRID 1916767Notes

Reaction equation

HRID 1916767 reaction equation
[CH3:1][N:2](C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C(N(CC)CC)C.[Cl:30][C:31]1[CH:36]=[CH:35][C:34]([C:37]2[CH:38]=[CH:39][C:40]([C:43]#[C:44][C:45]3[CH:46]=[CH:47][C:48]([O:54][CH2:55][CH2:56][N:57]4[CH2:61][CH2:60][CH2:59][CH2:58]4)=[C:49]([CH:53]=3)[C:50]([OH:52])=O)=[N:41][CH:42]=2)=[CH:33][CH:32]=1.CN>CN(C=O)C>[Cl:30][C:31]1[CH:32]=[CH:33][C:34]([C:37]2[CH:38]=[CH:39][C:40]([C:43]#[C:44][C:45]3[CH:46]=[CH:47][C:48]([O:54][CH2:55][CH2:56][N:57]4[CH2:58][CH2:59][CH2:60][CH2:61]4)=[C:49]([CH:53]=3)[C:50]([NH:2][CH3:1])=[O:52])=[N:41][CH:42]=2)=[CH:35][CH:36]=1

Participants

6

Reactant 4

HCID 6329MethylamineHCID 8471TriethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 59835898HCID 59835898, compound

Product 1

HCID 59835763HCID 59835763, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

80 mg (0.25 mmol) TBTU and 69 μL triethylamine are added to a solution of 112 mg (0.25 mmol) 5-[5-(4-chloro-phenyl)-pyridin-2-ylethynyl]-2-(2-pyrrolidin-1-yl-ethoxy)-benzoic acid (Example 22) in 5 mL DMF and the reaction mixture is stirred for 2 h at RT. Then 31 mg (1.0 mmol) methylamine are added and stirring is continued for a further 2 h at RT. The mixture is evaporated down i. vac., the residue is combined with dilute Na2CO3 solution, extracted exhaustively with DCM and the organic phase is dried over Na2SO4. After the desiccant and solvent have been eliminated the residue is purified by chromatography (silica gel, DCM to DCM/MeOH/NH3 7:3:0.3).

Workup

  1. stirringstirring
  2. waitis continued for a further 2 h at RT
  3. customThe mixture is evaporated down i
  4. extractionextracted exhaustively with DCM
  5. dry with materialthe organic phase is dried over Na2SO4
  6. customis purified by chromatography (silica gel, DCM to DCM/MeOH/NH3 7:3:0.3)

Sources & evidence

ORD record
ord-962af835db6044c88f7b337fef87713c
Source dataset
uspto-grants-2013_12
Patent number
US08618132B2

Reaction notes

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