Trifluoroacetic acid → HCID 52949210, compound

HRID 249898Notes

Reaction equation

HRID 249898 reaction equation
[Cl:1][C:2]1[CH:18]=[C:17]([C:19](=[O:29])[NH:20][CH:21]2[CH:26]3[CH2:27][CH2:28][N:23]([CH2:24][CH2:25]3)[CH2:22]2)[C:5]2[N:6]=[C:7]([NH:9]C(=O)OC(C)(C)C)[O:8][C:4]=2[CH:3]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[N:23]12[CH2:22][C@@H:21]([NH:20][C:19]([C:17]3[CH:18]=[C:2]([Cl:1])[CH:3]=[C:4]4[O:8][C:7]([NH2:9])=[N:6][C:5]=34)=[O:29])[CH:26]([CH2:27][CH2:28]1)[CH2:25][CH2:24]2

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66874405HCID 66874405, compound

Product 1

HCID 52949210HCID 52949210, compoundYield 38.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 6-chloro-4-(quinuclidine-8-yl-carbamoyl)benzoxazole-2-yl-carbamate (71 mg, 0.17 mmol) in CH2Cl2 (1 mL) was added TFA (1 mL). The reaction mixture stirred at room temperature for 3 h. The reaction mixture was concentrated under reduced pressure and the crude material was treated with concentrated ammonium hydroxide to adjust the pH to 7. The mixture was concentrated under reduced pressure and the crude material was purified by preparative TLC (90:9:1 CH2Cl2/CH3OH/concentrated NH4OH) to afford (S)—N-(quinuclidine-8-yl)-2-amino-6-chlorobenzoxazole-4-carboxamide (21 mg, 38%) as a white solid, which was converted to the hydrochloride salt following general procedure GP-D1. 1H NMR and MS consistent.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionthe crude material was treated with concentrated ammonium hydroxide
  3. concentrationThe mixture was concentrated under reduced pressure
  4. customthe crude material was purified by preparative TLC (90:9:1 CH2Cl2/CH3OH/concentrated NH4OH)

Sources & evidence

ORD record
ord-d79f61591dc546cc9bed256200dcffb1
Source dataset
uspto-grants-2011_01
Patent number
US07863271B2

Reaction notes

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