Tetrabutylammonium Fluoride → HCID 118413255, compound

HRID 929252Notes

Reaction equation

HRID 929252 reaction equation
[Si]([O:8][C@H:9]1[CH:13]2[O:14][CH2:15][C@@H:16]([O:17][C:18]3[NH:19][C:20]4[C:21]([N:39]=3)=[N:22][C:23]([C:27]3[S:28][C:29]5[CH:34]=[CH:33][N:32]=[C:31]([CH:35]6[CH2:37][CH2:36]6)[C:30]=5[N:38]=3)=[C:24]([Cl:26])[CH:25]=4)[CH:12]2[O:11][CH2:10]1)(C(C)(C)C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[Cl:26][C:24]1[CH:25]=[C:20]2[NH:19][C:18]([O:17][C@H:16]3[C@H:12]4[O:11][CH2:10][C@@H:9]([OH:8])[C@H:13]4[O:14][CH2:15]3)=[N:39][C:21]2=[N:22][C:23]=1[C:27]1[S:28][C:29]2[CH:34]=[CH:33][N:32]=[C:31]([CH:35]3[CH2:37][CH2:36]3)[C:30]=2[N:38]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 131735113HCID 131735113, compound

Product 1

HCID 118413255HCID 118413255, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 2-(2-(((3R,6R)-6-((tert-butyldimethylsilyl)-oxy)hexahydrofuro[3,2-b]furan-3-yl)oxy)-6-chloro-1H-imidazo[4,5-b]pyridin-5-yl)-4-cyclopropyl-thiazolo[4,5-c]pyridine (20.0 mg, 0.034 mmol) dissolved in anhydrous THF (0.3 mL) was added 1M TBAF in THF (0.07 mL, 0.070 mmol) and stirred at RT for 19 h. The reaction solution evaporated down under reduced pressure. Flash chromatography of the resulting residue utilizing a 4 g silica RediSep Rf® Gold column and employing a 0-15% MeOH/DCM gradient afforded the title compound. LC-MS: calculated for C21H18ClN5O4S 471.08 observed m/e: 472.01 (M+H)+ (Rt 1.02/1.8 min)

Workup

  1. customThe reaction solution evaporated down under reduced pressure

Sources & evidence

ORD record
ord-eb5e8a98d1e74c35b7c553e921d3b7b3
Source dataset
uspto-grants-2016_03
Patent number
US09290517B2

Reaction notes

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