2-Fluorophenyl isocyanate → 1-(2-Fluorophenyl)-3-(2-(quinolin-4-ylmethyl)-1,2,3,4-tetrahydroisoquinolin-5-yl)urea

HRID 2196589Notes

Reaction equation

HRID 2196589 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([CH2:11][N:12]2[CH2:21][CH2:20][C:19]3[C:18]([NH2:22])=[CH:17][CH:16]=[CH:15][C:14]=3[CH2:13]2)=[CH:3][CH:2]=1.[F:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[N:30]=[C:31]=[O:32]>O1CCCC1>[F:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[NH:30][C:31]([NH:22][C:18]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:19]=1[CH2:20][CH2:21][N:12]([CH2:11][C:4]1[C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[N:1]=[CH:2][CH:3]=1)[CH2:13]2)=[O:32]

Participants

4

Reactant 2

HCID 855882-Fluorophenyl isocyanateHCID 597568762-(Quinolin-4-ylmethyl)-1,2,3,4-tetrahydroisoquinolin-5-amine

Product 1

HCID 249591981-(2-Fluorophenyl)-3-(2-(quinolin-4-ylmethyl)-1,2,3,4-tetrahydroisoquinolin-5-yl)ureaYield 66%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

2-(Quinolin-4-ylmethyl)-1,2,3,4-tetrahydroisoquinolin-5-amine (80 mg, 0.277 mmol) was suspended in tetrahydrofuran (1 mL) then added a solution of 2-fluorophenylisocyanate (38 mg, 0.277 mmol) in tetrahydrofuran (0.5 mL). The reaction mixture was stirred at room temperature for 2 days. The product had precipitated from the reaction mixture and was collected on a glass frit, washing with minimal tetrahydrofuran then dichloromethane. The solid was dried under high vacuum to give 78 mg of 1-(2-fluorophenyl)-3-(2-(quinolin-4-ylmethyl)-1,2,3,4-tetrahydroisoquinolin-5-yl)urea as a white solid. MS (ESI, pos. ion) m/z: 427.1 (M+1).

Workup

  1. customThe product had precipitated from the reaction mixture
  2. customwas collected on a glass frit
  3. washwashing with minimal tetrahydrofuran
  4. customThe solid was dried under high vacuum

Sources & evidence

ORD record
ord-16f57f0b350a45faa134b40bf87457c7
Source dataset
uspto-grants-2012_12
Patent number
US08338455B2

Reaction notes

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