Trifluoroacetic acid methylene chloride → HCID 86694400, compound

HRID 535413Notes

Reaction equation

HRID 535413 reaction equation
C(O[C:6](=O)[N:7]([CH:9]([CH3:38])[C:10]([NH:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[C:20]([CH3:25])=[N:21][O:22][C:23]=2[CH3:24])=[C:15]([C:26]#[C:27][C:28]2[CH:29]=[C:30]3[C:35](=[CH:36][CH:37]=2)[CH:34]=[N:33][CH:32]=[CH:31]3)[N:14]=1)=[O:11])C)(C)(C)C.C(Cl)Cl.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:25][C:20]1[C:19]([C:16]2[CH:17]=[CH:18][C:13]([NH:12][C:10](=[O:11])[CH:9]([NH:7][CH3:6])[CH3:38])=[N:14][C:15]=2[C:26]#[C:27][C:28]2[CH:29]=[C:30]3[C:35](=[CH:36][CH:37]=2)[CH:34]=[N:33][CH:32]=[CH:31]3)=[C:23]([CH3:24])[O:22][N:21]=1

Participants

4

Reactant 2

HCID 21863450Trifluoroacetic acid methylene chlorideHCID 86694398HCID 86694398, compound

Product 1

HCID 86694400HCID 86694400, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of tert-butyl-N-[1-[[5-(3,5-dimethyl-1,2-oxazol-4-yl)-6-(2-isoquinolin-6-yl-ethynyl)pyridin-2-yl]amino]-1-oxopropan-2-yl]-N-methylcarbamate E2a (191 mg, 0.36 mmol) and DCM:TFA (9:1, 10 ml) is stirred at RT for 2 h. 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: 101 mg (65%). HPLC-MS: M+H=426; tR=1.30 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-f29fc9484f804f9ca74724d8533b946d
Source dataset
uspto-grants-2014_10
Patent number
US08859541B2

Reaction notes

Loading…