Trifluoroacetic acid → 7-[2-(2-Amino-thiazol-5-yl)-ethylamino]-thieno[3,2-b]pyridine-6-carbonitrile

HRID 1468995Notes

Reaction equation

HRID 1468995 reaction equation
C(OC(=O)[NH:7][C:8]1[S:9][C:10]([CH2:13][CH2:14][NH:15][C:16]2[C:21]([C:22]#[N:23])=[CH:20][N:19]=[C:18]3[CH:24]=[CH:25][S:26][C:17]=23)=[CH:11][N:12]=1)(C)(C)C.FC(F)(F)C(O)=O>ClCCl.C(OCC)(=O)C>[NH2:7][C:8]1[S:9][C:10]([CH2:13][CH2:14][NH:15][C:16]2[C:21]([C:22]#[N:23])=[CH:20][N:19]=[C:18]3[CH:24]=[CH:25][S:26][C:17]=23)=[CH:11][N:12]=1

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86640519{5-[2-(6-Cyano-thieno[3,2-b]pyridin-7-ylamino)-ethyl]-thiazol-2-yl}-carbamic acid tert-butyl ester

Product 1

HCID 866405207-[2-(2-Amino-thiazol-5-yl)-ethylamino]-thieno[3,2-b]pyridine-6-carbonitrileYield 88.5%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of {5-[2-(6-cyano-thieno[3,2-b]pyridin-7-ylamino)-ethyl]-thiazol-2-yl}-carbamic acid tert-butyl ester (36.1 mg, 0.09 mmol) and trifluoroacetic acid (1 ml) in 4 ml of dichloromethane was stirred at room temperature for 16 hr. Dichloromethane was evaporated, and the residue obtained was dissolved in ethyl acetate, washed with aqueous sodium bicarbonate solution, dried over MgSO4, filtered, and concentrated in vacuum to give a yellow crude product 24 mg. (89%). 1H NMR (300 MHz, CD3OD) δ 8.85 (s, 1H), 8.46 (d, J=5.4 Hz, 1H), 7.59 (d, J=5.7 Hz, 1H), 7.14 (s, 1H), 4.19 (t, J=7.2 Hz, 2H), 3.22 (t, J=7.2 Hz, 2H); LC-MS (ESI) m/z 302.0 (M+1).

Workup

  1. customDichloromethane was evaporated
  2. customthe residue obtained
  3. washwashed with aqueous sodium bicarbonate solution
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuum

Sources & evidence

ORD record
ord-ef74d435eb6149cd9cfc5815a60725df
Source dataset
uspto-grants-2015_04
Patent number
US09006252B2

Reaction notes

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