Hydrochloric Acid → HCID 57725526, compound

HRID 2370540Notes

Reaction equation

HRID 2370540 reaction equation
[OH:1][C@@H:2]1[CH2:7][CH2:6][CH2:5][CH2:4][C@H:3]1[NH:8][C:9]1[S:10][C:11]2[CH:17]=[C:16]([O:18][C:19]3[CH:24]=[CH:23][N:22]=[C:21]([C:25]([O:27]C(C)(C)C)=[O:26])[CH:20]=3)[CH:15]=[CH:14][C:12]=2[N:13]=1.Cl>C(#N)C>[OH:1][C@@H:2]1[CH2:7][CH2:6][CH2:5][CH2:4][C@H:3]1[NH:8][C:9]1[S:10][C:11]2[CH:17]=[C:16]([O:18][C:19]3[CH:24]=[CH:23][N:22]=[C:21]([C:25]([OH:27])=[O:26])[CH:20]=3)[CH:15]=[CH:14][C:12]=2[N:13]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 57725590HCID 57725590, compound

Product 1

HCID 57725526HCID 57725526, compoundYield 98.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To the solution of tert-butyl 4-(2-((1R,2R)-2-hydroxycyclohexylamino)benzo[d]thiazol-6-yloxy)picolinate (250 mg, 0566 mmol) in 10 ml of acetonitrile was added 6 M of hydrochloric acid (1 ml, 6 mmol). The reaction solution was stirred at room temperature for 1 hour and then at 60° C. for 2 hours. The crude reaction solution was concentrated and re-dissolved with 10 ml of acetonitrile. The resulting solution was evaporated in vaccuo to give light brown oily product 4-(2-((1R,2R)-2-hydroxycyclohexylamino)benzo[d]thiazol-6-yloxy)picolinic acid (215 mg, 0.56 mmol). ES/MS m/z 386.5 (MH+).

Workup

  1. waitat 60° C. for 2 hours
  2. customThe crude reaction solution
  3. concentrationwas concentrated
  4. dissolutionre-dissolved with 10 ml of acetonitrile
  5. customThe resulting solution was evaporated in vaccuo

Sources & evidence

ORD record
ord-9122217a2cd24d8f8fd35d803c8671a6
Source dataset
uspto-grants-2014_04
Patent number
US08710048B2

Reaction notes

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