Tetrabutylammonium Fluoride → HCID 178521007, compound

HRID 931234Notes

Reaction equation

HRID 931234 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[Si]([O:26][C:27]1([C:30]2[N:35]=[C:34]([C:36]3[NH:57][C:39]4=[N:40][C:41]([N:44]5[CH2:49][CH2:48][CH2:47][C@@H:46]([C:50]([N:52]6[CH2:56][CH2:55][CH2:54][CH2:53]6)=[O:51])[CH2:45]5)=[CH:42][CH:43]=[C:38]4[N:37]=3)[CH:33]=[CH:32][CH:31]=2)[CH2:29][CH2:28]1)(C(C)(C)C)(C)C>O1CCCC1>[OH:26][C:27]1([C:30]2[N:35]=[C:34]([C:36]3[NH:57][C:39]4=[N:40][C:41]([N:44]5[CH2:49][CH2:48][CH2:47][C@@H:46]([C:50]([N:52]6[CH2:53][CH2:54][CH2:55][CH2:56]6)=[O:51])[CH2:45]5)=[CH:42][CH:43]=[C:38]4[N:37]=3)[CH:33]=[CH:32][CH:31]=2)[CH2:29][CH2:28]1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 178455006HCID 178455006, compound

Product 1

HCID 178521007HCID 178521007, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Tetrabutylammonium fluoride (1M in tetrahydrofuran, 0.6 mL, 0.6 mmol) was added to a solution of (R)-(1-(2-(6-(1-((tert-butyldimethylsilyl)oxy)cyclopropyl)pyridin-2-yl)-3H-imidazo[4,5-b]pyridin-5-yl)piperidin-3-yl)(pyrrolidin-1-yl)methanone (89.7 mg, 0.2 mmol) in tetrahydrofuran (0.5 mL). The reaction mixture was stirred at room temperature for 40 min. The mixture was partitioned between water and ethyl acetate (3×). The combined organics were dried over sodium sulfate and concentrated under reduced pressure. The residue was purified via HPLC to afford the title compound. MS (ESI+) (M+H) 433.1; HPLC retention time 2.1091 min (Method B).

Workup

  1. customThe mixture was partitioned between water and ethyl acetate (3×)
  2. dry with materialThe combined organics were dried over sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified via HPLC

Sources & evidence

ORD record
ord-82a0b1b9f7ce488ea85a290525f8db78
Source dataset
uspto-grants-2016_03
Patent number
US09296745B2

Reaction notes

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