Trifluoroacetic acid → (S)-7-((3-methyloxetan-3-yl)ethynyl)-3-(6-methylpyridin-3-yl)-5'H-spiro[chromeno[2,3-b]pyridine-5,4'-thiazol]-2'-amine

HRID 335943Notes

Reaction equation

HRID 335943 reaction equation
[CH3:1][C:2]1([C:6]#[C:7][C:8]2[CH:9]=[C:10]3[C@@:21]4([CH2:25][S:24][C:23]([NH:26]C(=O)OC(C)(C)C)=[N:22]4)[C:20]4[C:15](=[N:16][CH:17]=[C:18]([C:34]5[CH:35]=[N:36][C:37]([CH3:40])=[CH:38][CH:39]=5)[CH:19]=4)[O:14][C:11]3=[CH:12][CH:13]=2)[CH2:5][O:4][CH2:3]1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:1][C:2]1([C:6]#[C:7][C:8]2[CH:9]=[C:10]3[C@@:21]4([CH2:25][S:24][C:23]([NH2:26])=[N:22]4)[C:20]4[C:15](=[N:16][CH:17]=[C:18]([C:34]5[CH:35]=[N:36][C:37]([CH3:40])=[CH:38][CH:39]=5)[CH:19]=4)[O:14][C:11]3=[CH:12][CH:13]=2)[CH2:3][O:4][CH2:5]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67436896(S)-tert-butyl 7-((3-methyloxetan-3-yl)ethynyl)-3-(6-methylpyridin-3-yl)-5'H-spiro[chromeno[2,3-b]pyridine-5,4'-thiazole]-2'-ylcarbamate

Product 1

HCID 58466250(S)-7-((3-methyloxetan-3-yl)ethynyl)-3-(6-methylpyridin-3-yl)-5'H-spiro[chromeno[2,3-b]pyridine-5,4'-thiazol]-2'-amineYield 75.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
50 °C

Procedure

(S)-Tert-butyl 7-((3-methyloxetan-3-yl)ethynyl)-3-(6-methylpyridin-3-yl)-5′H-spiro[chromeno[2,3-b]pyridine-5,4′-thiazole]-2′-ylcarbamate (0.027 g, 0.049 mmol) was taken up in 1.5 mL of DCM and TFA (0.057 mL, 0.735 mmol) was added. The reaction was heated to 50° C. and stirred for 2 h. The reaction was diluted with DCM and washed with saturated sodium bicarbonate solution. The aqueous layer was extracted with DCM, and the combined organic layers were dried with sodium sulfate, filtered, and concentrated to afford (S)-7-((3-methyloxetan-3-yl)ethynyl)-3-(6-methylpyridin-3-yl)-5′H-spiro[chromeno[2,3-b]pyridine-5,4′-thiazol]-2′-amine (0.017 g, 0.037 mmol, 37.6% yield) as a light yellow solid.

Workup

  1. washwashed with saturated sodium bicarbonate solution
  2. extractionThe aqueous layer was extracted with DCM
  3. dry with materialthe combined organic layers were dried with sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-1e695ad0fa514c5aa4f45859014d2fad
Source dataset
uspto-grants-2014_11
Patent number
US08883782B2

Reaction notes

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