Tetrabutylammonium Fluoride → HCID 58923884, compound

HRID 1364021Notes

Reaction equation

HRID 1364021 reaction equation
[Si]([O:8][CH:9]1[CH2:27][N:14]2[C:15]3[C:24]4[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=4)[N:18]=[C:17]([NH2:25])[C:16]=3[N:26]=[C:13]2[CH2:12][N:11]([S:28]([CH3:31])(=[O:30])=[O:29])[CH2:10]1)(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[NH2:25][C:17]1[C:16]2[N:26]=[C:13]3[CH2:12][N:11]([S:28]([CH3:31])(=[O:30])=[O:29])[CH2:10][CH:9]([OH:8])[CH2:27][N:14]3[C:15]=2[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[N:18]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 58923873HCID 58923873, compound

Product 1

HCID 58923884HCID 58923884, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-20 °C

Procedure

A suspension of 11-{[tert-butyl(dimethyl)silyl]oxy}-9-(methylsulfonyl)-9,10,11,12-tetrahydro-8H-[1,4]diazepino[1′,2′:1,2]imidazo[4,5-c]quinolin-6-amine (1.0 g, 2.2 mmol) in anhydrous THF (30 mL) was cooled to −20° C., and tetrabutylammonium fluoride (2.383 mL of a 1 M solution in THF) was slowly added. The reaction was stirred overnight, and a precipitate formed. The cold reaction mixture was filtered, and the isolated precipitate was washed with THF and dried under high vacuum to provide 313.7 mg of 6-amino-9-(methylsulfonyl)-9,10,11,12-tetrahydro-8H-[1,4]diazepino[1′,2′:1,2]imidazo[4,5-c]quinolin-11-ol as white crystals, mp 282-283° C.

Workup

  1. customa precipitate formed
  2. customThe cold reaction mixture
  3. filtrationwas filtered
  4. washthe isolated precipitate was washed with THF
  5. customdried under high vacuum

Sources & evidence

ORD record
ord-396b584d85394402830b34d1edbe98f0
Source dataset
uspto-grants-2011_02
Patent number
US07888349B2

Reaction notes

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