Trifluoroacetic acid → HCID 46850942, compound

HRID 1968337Notes

Reaction equation

HRID 1968337 reaction equation
C(OC([NH:8][C@H:9]([C:11]([O:13][CH2:14][CH2:15][O:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]2[C:28]([C:29]#[N:30])=[C:27]([NH:31][CH3:32])[N:26]=[C:25]([S:33][CH2:34][C:35]3[N:36]=[C:37]([C:40]4[CH:45]=[CH:44][C:43]([Cl:46])=[CH:42][CH:41]=4)[S:38][CH:39]=3)[C:24]=2[C:47]#[N:48])=[CH:19][CH:18]=1)=[O:12])[CH3:10])=O)(C)(C)C.[F:49][C:50]([F:55])([F:54])[C:51]([OH:53])=[O:52]>ClCCl>[F:49][C:50]([F:55])([F:54])[C:51]([OH:53])=[O:52].[NH2:8][C@H:9]([C:11]([O:13][CH2:14][CH2:15][O:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]2[C:28]([C:29]#[N:30])=[C:27]([NH:31][CH3:32])[N:26]=[C:25]([S:33][CH2:34][C:35]3[N:36]=[C:37]([C:40]4[CH:41]=[CH:42][C:43]([Cl:46])=[CH:44][CH:45]=4)[S:38][CH:39]=3)[C:24]=2[C:47]#[N:48])=[CH:19][CH:18]=1)=[O:12])[CH3:10]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59435624HCID 59435624, compound

Product 1

HCID 46850942HCID 46850942, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2.18 g (3.091 mmol) of 2-{4-(2-({(2-(4-chlorophenyl)-1,3-thiazol-4-yl)methyl}sulfanyl)-3,5-dicyano-6-(methylamino)pyridin-4-yl)phenoxy}ethyl N-(tert-butoxycarbonyl)-L-alaninate (Example 17A) were initially charged in 45 ml of dichloromethane. 4.76 ml (61.821 mmol) of trifluoroacetic acid were added, and the reaction solution was then stirred at RT overnight. The reaction solution was concentrated on a rotary evaporator and the residue was purified by preparative HPLC (acetonitrile/water+0.1% TFA). This gave 2.04 g (92% of theory) of the target compound.

Workup

  1. concentrationThe reaction solution was concentrated on a rotary evaporator
  2. customthe residue was purified by preparative HPLC (acetonitrile/water+0.1% TFA)

Sources & evidence

ORD record
ord-e31009e799bc44e5abb4ea86b2b9f4e5
Source dataset
uspto-grants-2013_04
Patent number
US08420825B2

Reaction notes

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