Trifluoroacetic acid → N-((S)-6-amino-4,5,6,7-tetrahydro-benzothiazol-2-yl)-3-[(4-cyano-phenylcarbamoyl)-methoxy]-benzamide

HRID 1524269Notes

Reaction equation

HRID 1524269 reaction equation
FC(F)(F)C(O)=O.C(OC(=O)[NH:14][C@H:15]1[CH2:45][CH2:44][C:18]2[N:19]=[C:20]([NH:22][C:23](=[O:43])[C:24]3[CH:29]=[CH:28][CH:27]=[C:26]([O:30][CH2:31][C:32](=[O:42])[NH:33][C:34]4[CH:39]=[CH:38][C:37]([C:40]#[N:41])=[CH:36][CH:35]=4)[CH:25]=3)[S:21][C:17]=2[CH2:16]1)(C)(C)C>C(Cl)Cl>[NH2:14][C@H:15]1[CH2:45][CH2:44][C:18]2[N:19]=[C:20]([NH:22][C:23](=[O:43])[C:24]3[CH:29]=[CH:28][CH:27]=[C:26]([O:30][CH2:31][C:32](=[O:42])[NH:33][C:34]4[CH:35]=[CH:36][C:37]([C:40]#[N:41])=[CH:38][CH:39]=4)[CH:25]=3)[S:21][C:17]=2[CH2:16]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86667841((S)-2-{3-[(4-cyano-phenylcarbamoyl)-methoxy]-benzoylamino}-4,5,6,7-tetrahydro-benzothiazol-6-yl)-carbamic acid tert-butyl ester

Product 1

HCID 56598835N-((S)-6-amino-4,5,6,7-tetrahydro-benzothiazol-2-yl)-3-[(4-cyano-phenylcarbamoyl)-methoxy]-benzamideYield 60.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Add trifluoroacetic acid (1.0 mL, 14 mmol) to a solution of ((S)-2-{3-[(4-cyano-phenylcarbamoyl)-methoxy]-benzoylamino}-4,5,6,7-tetrahydro-benzothiazol-6-yl)-carbamic acid tert-butyl ester (0.14 g, 0.26 mmol) in methylene chloride (10 mL). Stir the mixture at room temperature for 15 h then concentrate under reduced pressure. Purify the residue by preparative reverse phase HPLC using acetonitrile/water with 0.1% trifluoroacetic acid additive as the eluent to provide 0.07 g of the title compound as a white powder. MS, electrospray 448.75 (M+H), rt. 1.21 min.

Workup

  1. concentrationthen concentrate under reduced pressure
  2. customPurify the residue by preparative reverse phase

Sources & evidence

ORD record
ord-0513f659356447598807758bb99955f5
Source dataset
uspto-grants-2015_07
Patent number
US09079880B2

Reaction notes

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