Tetrabutylammonium Fluoride → HCID 71280658, compound

HRID 1497919Notes

Reaction equation

HRID 1497919 reaction equation
[F:1][C:2]1([F:42])[CH2:5][CH:4]([C:6]2[O:10][N:9]=[C:8]([C:11]3[CH:12]=[CH:13][C:14]([CH3:41])=[C:15]([NH:17][C:18]([C:20]4[N:24]5[CH:25]=[C:26]([CH2:29][O:30][Si](C(C)C)(C(C)C)C(C)C)[CH:27]=[CH:28][C:23]5=[N:22][CH:21]=4)=[O:19])[CH:16]=3)[N:7]=2)[CH2:3]1.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[F:42][C:2]1([F:1])[CH2:5][CH:4]([C:6]2[O:10][N:9]=[C:8]([C:11]3[CH:12]=[CH:13][C:14]([CH3:41])=[C:15]([NH:17][C:18]([C:20]4[N:24]5[CH:25]=[C:26]([CH2:29][OH:30])[CH:27]=[CH:28][C:23]5=[N:22][CH:21]=4)=[O:19])[CH:16]=3)[N:7]=2)[CH2:3]1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 71280509HCID 71280509, compound

Product 1

HCID 71280658HCID 71280658, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-(5-(5-(3,3-difluorocyclobutyl)-1,2,4-oxadiazol-3-yl)-2-methylphenyl)-6-(((triisopropylsilyl)oxy)methyl)imidazo[1,2-a]pyridine-3-carboxamide (64) (230 mg, 0.39 mmol) in THF (5 mL), was added TBAF (1M in THF, 0.43 mL) and the resulting mixture was stirred for 1 hour. THF was removed and the residue was added to a mixture of water (10 mL), MeOH (5 mL) and EtOAc (5 mL). Organic solvents were removed slowly to give a precipitate which was filtered and dried to afford N-(5-(5-(3,3-difluorocyclobutyl)-1,2,4-oxadiazol-3-yl)-2-methylphenyl)-6-(hydroxymethyl)imidazo[1,2-a]pyridine-3-carboxamide (F37). 1H NMR (400 MHz, CDCl3) δ 9.39 (m, 1H), 8.42 (d, J=1.6 Hz, 1H), 8.04 (s, 1H), 7.70 (dd, J=1.7, 7.9 Hz, 1H), 7.60 (d, J=9.2 Hz, 1H), 7.42 (s, 1H), 7.36 (dd, J=1.7, 9.2 Hz, 1H), 7.23 (d, J=8.1 Hz, 1H), 4.63 (d, J=5.7 Hz, 2H), 3.63-3.41 (m, 1H), 3.09-2.85 (m, 4H), 2.28 (s, 3H), 1.82 (t, J=5.9 Hz, 1H). MS m/z 440.1 (M+1)+.

Workup

  1. customTHF was removed
  2. additionthe residue was added to a mixture of water (10 mL), MeOH (5 mL) and EtOAc (5 mL)
  3. customOrganic solvents were removed slowly
  4. customto give a precipitate which
  5. filtrationwas filtered
  6. customdried

Sources & evidence

ORD record
ord-cb18159e3da7467a91c8efafaf9026cc
Source dataset
uspto-grants-2015_12
Patent number
US09199981B2

Reaction notes

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