Boron trifluoride etherate → HCID 135507194, compound

HRID 859031Notes

Reaction equation

HRID 859031 reaction equation
C[O:2][C:3]1[C:8](OC)=[C:7]([C:11]([F:14])([F:13])[F:12])[CH:6]=[CH:5][C:4]=1[C:15]1[N:20]=[CH:19][N:18]=[C:17]([O:21][C:22]2[C:27]3[N:28]=[C:29]([NH2:31])[S:30][C:26]=3[CH:25]=[CH:24][CH:23]=2)[CH:16]=1.B(F)(F)F.CCOCC>ClCCl>[NH2:31][C:29]1[S:30][C:26]2[CH:25]=[CH:24][CH:23]=[C:22]([O:21][C:17]3[N:18]=[CH:19][N:20]=[C:15]([C:4]4[CH:5]=[CH:6][C:7]([C:11]([F:14])([F:13])[F:12])=[CH:8][C:3]=4[OH:2])[CH:16]=3)[C:27]=2[N:28]=1

Participants

4

Reactant 2

HCID 8000Boron trifluoride etherateHCID 86592066HCID 86592066, compound

Product 1

HCID 135507194HCID 135507194, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

To a 100-mL, round-bottomed flask containing a solution of 4-[6-(2-methoxy-methoxy-4-trifluoromethyl-phenyl)-pyrimidin-4-yloxy]-benzothiazol-2-ylamine, (Example 135(c)), (1.8 g, 3.9 mmol) in dichloromethane (39 mL) was added boron trifluoride diethyl etherate (1.5 mL, 12 mmol, Aldrich) with stirring at −78° C. The reaction mixture was then stirred at 0° C. for 1 h and at room temperature for 3 h. The mixture was quenched with satd sodium bicarbonate at 0° C. and extracted with dichloromethane (2×100 mL). The combined organic extracts were dried over Na2SO4, filtered and concentrated in vacuum. The crude material was purified by silica gel chromatography (gradient: 0–3% 2 N ammonia in methanol/dichloromethane) to yield the title compound as an amorphous, white solid. MS (ESI, pos. ion.) m/z: 406 (M+1).

Workup

  1. stirringThe reaction mixture was then stirred at 0° C. for 1 h and at room temperature for 3 h
  2. customThe mixture was quenched with satd sodium bicarbonate at 0° C.
  3. extractionextracted with dichloromethane (2×100 mL)
  4. dry with materialThe combined organic extracts were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuum
  7. customThe crude material was purified by silica gel chromatography (gradient: 0–3% 2 N ammonia in methanol/dichloromethane)

Sources & evidence

ORD record
ord-6ac0b04c5ce94905b5e161b2e41db2e6
Source dataset
uspto-grants-2006_12
Patent number
US07148221B2

Reaction notes

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