Trifluoroacetic acid → HCID 89689808, compound

HRID 877559Notes

Reaction equation

HRID 877559 reaction equation
[C:1]([N:4]([C:12]1[N:13]=[C:14]([C:18]2[CH:19]=[N:20][C:21]([NH:28][C:29]3[CH:37]=[CH:36][C:32]4[N:33]=[CH:34][S:35][C:31]=4[CH:30]=3)=[CH:22][C:23]=2[NH:24][CH:25]([CH3:27])[CH3:26])[O:15][C:16]=1[CH3:17])C(=O)OC(C)(C)C)(=[O:3])[CH3:2].C(O)(C(F)(F)F)=O>C(Cl)Cl>[S:35]1[C:31]2[CH:30]=[C:29]([NH:28][C:21]3[N:20]=[CH:19][C:18]([C:14]4[O:15][C:16]([CH3:17])=[C:12]([NH:4][C:1](=[O:3])[CH3:2])[N:13]=4)=[C:23]([NH:24][CH:25]([CH3:27])[CH3:26])[CH:22]=3)[CH:37]=[CH:36][C:32]=2[N:33]=[CH:34]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 89689617HCID 89689617, compound

Product 1

HCID 89689808HCID 89689808, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of tert-butyl acetyl(2-(6-(benzo[d]thiazol-6-ylamino)-4-(isopropylamino)pyridin-3-yl)-5-methyloxazol-4-yl)carbamate (35) (30 mg, 0.057 mmol) in DCM (5 mL) was treated with TFA (0.230 mmol) and stirred at room temperature for 3 h. The reaction mixture was concentrated and azeotroped with chloroform three times to obtain gummy solid. The crude material obtained was purified by prep HPLC to furnish N-(2-(6-(benzo[d]thiazol-6-ylamino)-4-(isopropylamino)pyridin-3-yl)-5-methyloxazol-4-yl)acetamide. 1H NMR: 400 MHz, CD3OD: δ 1.33 (d, J=6.40 Hz, 6H), 2.16 (s, 3H), 2.35 (s, 3H), 3.73-3.79 (m, 1H), 6.14 (s, 1H), 7.52 (dd, J=2.40, 8.80 Hz, 1H), 7.97 (d, J=8.80 Hz, 1H), 8.38 (d, J=2.00 Hz, 1H), 8.49 (s, 1H), 9.07 (s, 1H). LC/MS: Ascentis Express C18, 5×2.1 mm, 2.7 μm; Solvent A=2% ACN: 98% H2O: 10 mM NH4COOH; Solvent B=98% ACN: 2% H2O: 10 mM NH4COOH; gradient 0-100% B over 1.5 min; retention time: 1.823 min; LCMS (ES-API), m/z 423.2 (M+H). HPLC: XBridge Phenyl (150×4.6 mm), 3.5 micron; Solvent A=5% ACN: 95% H2O: 0.05% TFA pH=2.5; Solvent B=95% ACN: 5% H2O: 0.05% TFA pH=2.5; gradient 0-100% B over 15 min (23 min run time); Flow rate: 1.0 μL/min; Retention time: 6.484 min; Purity: 95.1%.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customazeotroped with chloroform three times
  3. customto obtain gummy solid
  4. customThe crude material obtained
  5. customwas purified by prep HPLC

Sources & evidence

ORD record
ord-7ea0c1a84ac1481a8549322205bdc2ae
Source dataset
uspto-grants-2015_03
Patent number
US08987311B2

Reaction notes

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