Trifluoroacetic acid methylene chloride → N-methyl-N-[6-[2-(methylamino)propanoylamino]-2-(2-phenyl-ethynyl)pyridin-3-yl]oxane-4-carboxamide

HRID 535440Notes

Reaction equation

HRID 535440 reaction equation
C(O[C:6](=O)[N:7](C)[CH:8]([CH3:36])[C:9]([NH:11][C:12]1[CH:17]=[CH:16][C:15]([N:18]([CH3:27])[C:19]([CH:21]2[CH2:26][CH2:25][O:24][CH2:23][CH2:22]2)=[O:20])=[C:14]([C:28]#[C:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[N:13]=1)=[O:10])(C)(C)C.C(Cl)Cl.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:27][N:18]([C:15]1[C:14]([C:28]#[C:29][C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)=[N:13][C:12]([NH:11][C:9](=[O:10])[CH:8]([NH:7][CH3:6])[CH3:36])=[CH:17][CH:16]=1)[C:19]([CH:21]1[CH2:22][CH2:23][O:24][CH2:25][CH2:26]1)=[O:20]

Participants

4

Reactant 2

HCID 21863450Trifluoroacetic acid methylene chlorideHCID 86694429tert-butyl-N-methyl-N-[1-[[5-[methyl(oxane-4-carbonyl)amino]-6-(2-phenyl-ethynyl)pyridin-2-yl]amino]-1-oxopropan-2-yl]carbamate

Product 1

HCID 86694430N-methyl-N-[6-[2-(methylamino)propanoylamino]-2-(2-phenyl-ethynyl)pyridin-3-yl]oxane-4-carboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of tert-butyl-N-methyl-N-[1-[[5-[methyl(oxane-4-carbonyl)amino]-6-(2-phenylethynyl)pyridin-2-yl]amino]-1-oxopropan-2-yl]carbamate F5b (5 mg) and DCM:TFA (9:1, 1 ml) is stirred at RT for 100 minutes. The mixture is diluted with DCM and extracted with a saturated aqueous solution of NaHCO3. The combined organic layers are dried over MgSO4 and concentrated in vacuo. The product is purified by RP HPLC. Yield: 7 mg. HPLC-MS: M+H=421; tR=1.33 min (*Method—1).

Workup

  1. extractionextracted with a saturated aqueous solution of NaHCO3
  2. dry with materialThe combined organic layers are dried over MgSO4
  3. concentrationconcentrated in vacuo
  4. customThe product is purified by RP HPLC

Sources & evidence

ORD record
ord-f6bc19281df84d8ca770c1dda30b25c2
Source dataset
uspto-grants-2014_10
Patent number
US08859541B2

Reaction notes

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