Trifluoroacetic acid → HCID 117598555, compound

HRID 1423255Notes

Reaction equation

HRID 1423255 reaction equation
C(OC(=O)[NH:7][C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]([O:18][C:19]2[CH:24]=[CH:23][N:22]=[C:21]([NH:25][C:26]3[CH:31]=[C:30]([C:32](=[O:44])[NH:33][CH2:34][CH2:35][O:36][CH2:37][CH2:38][O:39][CH2:40][CH2:41][O:42][CH3:43])[CH:29]=[C:28]([C:45]#[CH:46])[CH:27]=3)[N:20]=2)=[CH:10][CH:9]=1)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:7][C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]([O:18][C:19]2[CH:24]=[CH:23][N:22]=[C:21]([NH:25][C:26]3[CH:31]=[C:30]([CH:29]=[C:28]([C:45]#[CH:46])[CH:27]=3)[C:32]([NH:33][CH2:34][CH2:35][O:36][CH2:37][CH2:38][O:39][CH2:40][CH2:41][O:42][CH3:43])=[O:44])[N:20]=2)=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 131732230tert-Butyl(4((2-((3-ethynyl-5-((2-(2-(2-methoxyethoxy)ethoxy)ethyl)carbamoyl)phenyl)-amino)pyrimidin-4-yl)oxy)naphthalen-1-yl)carbamate

Product 1

HCID 117598555HCID 117598555, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of the product from step (v) above (540 mg, 0.825 mmol) in DCM (8 mL) was added TFA (3.2 mL, 41.5 mmol). The reaction was stirred at it for 1 h. The solution was concentrated in vacuo and the resulting oil dissolved in the minimum of MeOH and loaded onto SCX. The column was eluted with MeOH (3 column volumes), then 1% NH3 in MeOH (3 column volumes). The product-containing portion was concentrated in vacuo to afford the sub-title compound (405 mg) as a light, brown foam.

Workup

  1. concentrationThe solution was concentrated in vacuo
  2. dissolutionthe resulting oil dissolved in the minimum of MeOH
  3. washThe column was eluted with MeOH (3 column volumes)
  4. concentrationThe product-containing portion was concentrated in vacuo

Sources & evidence

ORD record
ord-8dcb8a98c0ca473894f3976f8c345276
Source dataset
uspto-grants-2015_01
Patent number
US08927563B2

Reaction notes

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