Ammonium Chloride → 2-(3-ethynyl-quinolin-6-yloxy)-N-(1-hydroxymethyl-cyclobutyl)-2-methylsulfanyl-acetamide

HRID 1892055

Reaction equation

HRID 1892055 reaction equation
[C:1]([C:3]1[CH:4]=[N:5][C:6]2[C:11]([CH:12]=1)=[CH:10][C:9]([O:13][CH:14]([S:18][CH3:19])[C:15]([OH:17])=O)=[CH:8][CH:7]=2)#[CH:2].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.[NH2:42][C:43]1([CH2:47][OH:48])[CH2:46][CH2:45][CH2:44]1.[NH4+].[Cl-]>CC#N.CCN(CC)CC>[C:1]([C:3]1[CH:4]=[N:5][C:6]2[C:11]([CH:12]=1)=[CH:10][C:9]([O:13][CH:14]([S:18][CH3:19])[C:15]([NH:42][C:43]1([CH2:47][OH:48])[CH2:46][CH2:45][CH2:44]1)=[O:17])=[CH:8][CH:7]=2)#[CH:2]

Participants

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 21624254(1-Aminocyclobutyl)methanolHCID 59565474(3-Ethynyl-quinolin-6-yloxy)-methylsulfanyl-acetic acid

Product 1

HCID 595653282-(3-ethynyl-quinolin-6-yloxy)-N-(1-hydroxymethyl-cyclobutyl)-2-methylsulfanyl-acetamideYield 331.1%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8471TriethylamineSolvent

Procedure

To a solution of (3-ethynyl-quinolin-6-yloxy)-methylsulfanyl-acetic acid (1.10 g) in CH3CN (40 ml) was added Et3N (2.25 ml), AHOBT (0.06 g), TBTU (1.50 g) and (1-amino-cyclobutyl)-methanol (0.06 g) at room temperature, under nitrogen atmosphere. The mixture was stirred at the same temperature during 1 hour, then poured into sat aq NH4Cl and extracted with ethyl acetate (2×20 ml). The organic phase was separated and washed with aq Na2S2O3 and sat. aq. NaCl then dried over anhydrous sodium sulphate, filtered and evaporated under vacuum. Purification by flash chromatography (ethyl acetate/cyclohexane, 2/1) gave 2-(3-ethynyl-quinolin-6-yloxy)-N-(1-hydroxymethyl-cyclobutyl)-2-methylsulfanyl-acetamide (0.70 g) as a yellow oil.

Workup

  1. additionpoured
  2. extractionextracted with ethyl acetate (2×20 ml)
  3. customThe organic phase was separated
  4. washwashed with aq Na2S2O3 and sat. aq. NaCl
  5. dry with materialthen dried over anhydrous sodium sulphate
  6. filtrationfiltered
  7. customevaporated under vacuum
  8. customPurification by flash chromatography (ethyl acetate/cyclohexane, 2/1)

Sources & evidence

ORD record
ord-d63b4808df2e48fd8b1f5b4f5eca3baf
Source dataset
uspto-grants-2013_08
Patent number
US08507509B2

Linked notes

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