Tetrabutylammonium Fluoride → HCID 178508371, compound

HRID 389606Notes

Reaction equation

HRID 389606 reaction equation
[F:1][C:2]([F:43])([F:42])[C:3]1[CH:4]=[C:5]([C:13]2[O:41][C:16]3=[C:17]([NH2:40])[N:18]=[CH:19][C:20]([C:21]4[CH:22]=[N:23][N:24]([CH:26]5[CH2:31][CH2:30][CH:29]([O:32][Si](C(C)(C)C)(C)C)[CH2:28][CH2:27]5)[CH:25]=4)=[C:15]3[CH:14]=2)[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1.CCOC(C)=O>[NH2:40][C:17]1[N:18]=[CH:19][C:20]([C:21]2[CH:22]=[N:23][N:24]([C@H:26]3[CH2:31][CH2:30][C@H:29]([OH:32])[CH2:28][CH2:27]3)[CH:25]=2)=[C:15]2[CH:14]=[C:13]([C:5]3[CH:6]=[C:7]([C:9]([F:10])([F:11])[F:12])[CH:8]=[C:3]([C:2]([F:43])([F:1])[F:42])[CH:4]=3)[O:41][C:16]=12

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 86662426HCID 86662426, compound

Product 1

HCID 178508371HCID 178508371, compoundYield 38.8%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2-[3,5-bis(trifluoromethyl)phenyl]-4-[1-(4-{[tert-butyl(dimethyl)silyl]oxy}cyclohexyl)-1H-pyrazol-4-yl]furo[2,3-c]pyridin-7-amine (104 mg) in THF (2 mL) was treated with tetra-n-butylammonium fluoride (2.7 M in water, 0.20 mL, 0.56 mmol) and stirred at RT overnight. The solution was diluted with EtOAc and washed with brine. The aqueous phase was extracted with EtOAc and the combined organic fractions were dried over sodium sulfate and concentrated. Purification of the residue by ISCO chromatography (0 to 5% 7 N NH3/MeOH:EtOAc) afforded 33 mg (35%) of the title compound as a yellow solid. 1H NMR (400 MHz, CD3OD): δ 1.48-1.60 (m, 2H) 2.01 (qd, J=12.7, 3.2 Hz, 2H) 2.10-2.26 (m, 4H) 3.73 (tt, J=10.9, 4.1 Hz, 1H) 4.26 (tt, J=11.9, 3.9 Hz, 1H) 7.88 (s, 1H) 7.91-7.94 (m, 2H) 8.00-8.03 (m, 1H) 8.12-8.15 (m, 1H) 8.67 (s, 2H); MS (ESI): 510.34 [M+H]+; HPLC tR=1.16 min (TOF: polar—3 min).

Workup

  1. washwashed with brine
  2. extractionThe aqueous phase was extracted with EtOAc
  3. dry with materialthe combined organic fractions were dried over sodium sulfate
  4. concentrationconcentrated
  5. customPurification of the residue by ISCO chromatography (0 to 5% 7 N NH3/MeOH:EtOAc)

Sources & evidence

ORD record
ord-8d8e32368e6049ce95f65a455d670f44
Source dataset
uspto-grants-2013_02
Patent number
US08378104B2

Reaction notes

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