Ammonia → HCID 86689151, compound

HRID 1752467Notes

Reaction equation

HRID 1752467 reaction equation
[Br:1][C:2]1[N:7]=[C:6]([C@:8]([NH:18][S@](C(C)(C)C)=O)([CH2:14][CH2:15][O:16][CH3:17])[C:9]([F:13])([F:12])[CH2:10][OH:11])[C:5]([F:25])=[CH:4][CH:3]=1.Cl.C(OCC)C.N>CO>[NH2:18][C@@:8]([C:6]1[C:5]([F:25])=[CH:4][CH:3]=[C:2]([Br:1])[N:7]=1)([CH2:14][CH2:15][O:16][CH3:17])[C:9]([F:12])([F:13])[CH2:10][OH:11]

Participants

6

Reactant 4

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 86689149HCID 86689149, compound

Product 1

HCID 86689151HCID 86689151, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution of (S)-2-methyl-propane-2-sulfinic acid [(R)-1-(6-bromo-3-fluoro-pyridin-2-yl)-2,2-difluoro-3-hydroxy-1-(2-methoxy-ethyl)-propyl]amide (1.50 g, 3.33 mmol) in methanol (8.4 ml) was added 2M HCl in diethyl ether (6.56 ml, 13.11 mmol). The reaction mixture was stirred for 1.5 h at room temperature. 7 M ammonia in methanol (2.7 ml) was added to the reaction mixture and the resulting colourless suspension was evaporated in vacuo. The remaining solid was triturated with warm dichloromethane, cooled to rt, filtered and rinsed with dichloromethane. The filtrate was evaporated affording the title compound which was used without purification in the next step. 1.42 g colourless, viscous oil. 100% yield.

Workup

  1. customthe resulting colourless suspension was evaporated in vacuo
  2. customThe remaining solid was triturated with warm dichloromethane
  3. temperaturecooled to rt
  4. filtrationfiltered
  5. washrinsed with dichloromethane
  6. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-79df0533627640aea220e1d24e1bde14
Source dataset
uspto-grants-2015_10
Patent number
US09163011B2

Reaction notes

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