Ethanol → HCID 57967263, compound

HRID 1401351Notes

Reaction equation

HRID 1401351 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([N:11]=[C:12]=[S:13])=[O:10])=[CH:4][CH:3]=1.CCO.[NH2:17][C:18]1[CH:52]=[CH:51][C:21]([O:22][C:23]2[CH:28]=[CH:27][N:26]=[C:25]3[CH:29]=[C:30]([C:32]4[N:37]=[CH:36][C:35]([CH2:38][N:39]([CH2:47][CH2:48][O:49][CH3:50])[C:40](=[O:46])[O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[CH:34][CH:33]=4)[S:31][C:24]=23)=[C:20]([F:53])[CH:19]=1>C1(C)C=CC=CC=1>[F:53][C:20]1[CH:19]=[C:18]([NH:17][C:12]([NH:11][C:9](=[O:10])[CH2:8][C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=2)=[S:13])[CH:52]=[CH:51][C:21]=1[O:22][C:23]1[CH:28]=[CH:27][N:26]=[C:25]2[CH:29]=[C:30]([C:32]3[N:37]=[CH:36][C:35]([CH2:38][N:39]([CH2:47][CH2:48][O:49][CH3:50])[C:40](=[O:46])[O:41][C:42]([CH3:45])([CH3:43])[CH3:44])=[CH:34][CH:33]=3)[S:31][C:24]=12

Participants

5

Reactant 3

HCID 702Ethanol3×HCID 231532482-(4-Fluorophenyl)acetyl isothiocyanate2×HCID 579194724-[[2-[5-[[Boc(2-methoxyethyl)amino]methyl]-2-pyridyl]-7-thieno[3,2-b]pyridyl]oxy]-3-fluoroaniline

Product 1

HCID 57967263HCID 57967263, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent3×

Procedure

To a suspension of isothiocyanate 2 (5.50 g, 28.2 mmol) in a mixture of toluene (20 mL)/EtOH (20 mL) in a 500 mL round-bottom flask was added aniline 13 (10 g, 19.06 mmol) in a mixture of toluene (50 mL)/EtOH (50 mL). After 30 min, additional amount of isothiocyanate 2 (1 g, 5.12 mmol) in a mixture toluene (5 mL)/EtOH (5 mL) was added to the reaction mixture which was stirred at r.t. for an additional 45 min. The reaction mixture was concentrated under reduced pressure and the residue was co-evaporated with MeOH (40 mL) to dryness. Finally MeOH (80 mL) was added to the dry residue to produce a precipitate that was stirred at room temperature for 14 h, collected by filtration, dried for 2 h under vacuum to afford 14 as beige solid (7 g, 51% yield). MS (m/z): 720.3 (M+1)

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionFinally MeOH (80 mL) was added to the dry residue
  3. customto produce a precipitate that
  4. stirringwas stirred at room temperature for 14 h
  5. filtrationcollected by filtration
  6. customdried for 2 h under vacuum

Sources & evidence

ORD record
ord-11bbaa5d71c842db9d865af7a0f863fe
Source dataset
uspto-grants-2014_12
Patent number
US08907091B2

Reaction notes

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