Tetrabutylammonium Fluoride → HCID 178493861, compound

HRID 1259511Notes

Reaction equation

HRID 1259511 reaction equation
[Si]([O:8][CH2:9][CH:10]1[O:15][CH2:14][CH2:13][N:12]([CH2:16][CH2:17][CH2:18][O:19][C:20]2[CH:21]=[CH:22][C:23]3[C:24]4[N:25]([CH2:41][CH2:42][N:43]=4)[C:26]([NH:32][C:33](=[O:40])[C:34]4[CH:39]=[CH:38][CH:37]=[N:36][CH:35]=4)=[N:27][C:28]=3[C:29]=2[O:30][CH3:31])[CH2:11]1)(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1.O>[OH:8][CH2:9][CH:10]1[O:15][CH2:14][CH2:13][N:12]([CH2:16][CH2:17][CH2:18][O:19][C:20]2[CH:21]=[CH:22][C:23]3[C:24]4[N:25]([CH2:41][CH2:42][N:43]=4)[C:26]([NH:32][C:33](=[O:40])[C:34]4[CH:39]=[CH:38][CH:37]=[N:36][CH:35]=4)=[N:27][C:28]=3[C:29]=2[O:30][CH3:31])[CH2:11]1

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 178493862HCID 178493862, compound

Product 1

HCID 178493861HCID 178493861, compoundYield 47%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

N-(8-{3-[2-({[tert-butyl(dimethyl)silyl]oxy}methyl)morpholin-4-yl]propoxy}-7-methoxy-2,3-dihydroimidazo[1,2-c]quinazolin-5-yl)nicotinamide (260 mg, 0.43 mmol) was suspended in THF (2 mL) and treated with a solution of tetra-n-butylammonium fluoride (1N, 0.64 mL, 0.64 mmol) in THF. The resulting mixture was stirred at rt for 4 h and was then diluted with water and extracted with 20% isopropanol/80% chloroform, dried (MgSO4) and concentrated under reduced pressure. The residue was then triturated with methanol and filtered to give the product as a solid (100 mg, 47%): HPLC MS RT=0.19 min, MH+=495.2; 1H NMR (DMSO-d6) δ: 12.7 (1H, s), 9.33 (1H, dd), 8.73 (1H, dd), 8.46 (1H, dt), 7.60 (1H, d), 7.54-7.49 (1H, m), 7.06 (1H, d) 4.66 (1H, t), 4.20-4.09 (4H, m), 4.07-3.98 (2H, m) 3.93 (3H, s), 3.76 (1H, br d), 3.48 (1H, td), 3.42-3.26 (4H, m), 2.83 (1H, d), 2.70 (1H, d), 2.47 (2H, t), 2.03-1.91 (3H, m).

Workup

  1. extractionextracted with 20% isopropanol/80% chloroform
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was then triturated with methanol
  5. filtrationfiltered

Sources & evidence

ORD record
ord-d5ab2a5c61774771afcb470b2c727c4c
Source dataset
uspto-grants-2013_06
Patent number
US08466283B2

Reaction notes

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