Ammonium Chloride → HCID 68231757, compound

HRID 869181Notes

Reaction equation

HRID 869181 reaction equation
[Si]([O:8][CH2:9][C:10]1[S:14][C:13]([C:15]2[N:20]=[N:19][C:18]([N:21]([CH2:29][C:30]3([C:34]4[C:39]([F:40])=[CH:38][CH:37]=[CH:36][N:35]=4)[CH2:33][CH2:32][CH2:31]3)[C:22](=[O:28])[O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[CH:17][CH:16]=2)=[N:12][CH:11]=1)(C(C)(C)C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-].[Cl-].[NH4+]>C1COCC1>[F:40][C:39]1[C:34]([C:30]2([CH2:29][N:21]([C:18]3[N:19]=[N:20][C:15]([C:13]4[S:14][C:10]([CH2:9][OH:8])=[CH:11][N:12]=4)=[CH:16][CH:17]=3)[C:22](=[O:28])[O:23][C:24]([CH3:27])([CH3:26])[CH3:25])[CH2:33][CH2:32][CH2:31]2)=[N:35][CH:36]=[CH:37][CH:38]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 2724141Tetrabutylammonium FluorideHCID 68232116HCID 68232116, compound

Product 1

HCID 68231757HCID 68231757, compoundYield 49.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of t-butyl 6-(5-((tert-butyldimethylsilyloxy)methyl)thiazol-2-yl)pyridazin-3-yl((1-(3-fluoropyridin-2-yl)cyclobutyl)methyl)carbamate (112.5 g, 0.19 mol) in THF (1000 mL) was added TBAF (105 mL, 0.29 mol, 75% w/w). The reaction was stirred for 30 min followed by the addition of ammonium chloride (200 mL). The organic layer was separated, washed with brine (300 mL×3), and concentrated (this wash was repeated once). Ethyl acetate was added to the oil, resulting in a white solid. Filtration of the solid afforded 44 g of t-butyl (1-(3-fluoropyridin-2-yl)cyclobutyl)methyl(6-(5-(hydroxymethyl)thiazol-2-yl)pyridazin-3-yl)carbamate.

Workup

  1. customThe organic layer was separated
  2. washwashed with brine (300 mL×3)
  3. concentrationconcentrated (this wash
  4. additionEthyl acetate was added to the oil
  5. customresulting in a white solid
  6. filtrationFiltration of the solid

Sources & evidence

ORD record
ord-3e5f602025e74d0897d7717d946b26cd
Source dataset
uspto-grants-2015_03
Patent number
US08969346B2

Reaction notes

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