Phenyl isocyanate → (S)-(6-cyano-1,2,3,4-tetrahydroquinolin-3-yl)-3-phenylurea

HRID 2234254Notes

Reaction equation

HRID 2234254 reaction equation
[NH2:1][C@H:2]1[CH2:11][C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:12]#[N:13])[CH:9]=2)[NH:4][CH2:3]1.[C:14]1([N:20]=[C:21]=[O:22])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C(Cl)Cl>[C:12]([C:8]1[CH:9]=[C:10]2[C:5](=[CH:6][CH:7]=1)[NH:4][CH2:3][C@@H:2]([NH:1][C:21]([NH:20][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:22])[CH2:11]2)#[N:13]

Participants

4

Reactant 2

HCID 7672Phenyl isocyanateHCID 66757521(S)-3-Amino-1,2,3,4-tetrahydroquinoline-6-carbonitrile

Product 1

HCID 68581279(S)-(6-cyano-1,2,3,4-tetrahydroquinolin-3-yl)-3-phenylureaYield 97%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (S)-3-amino-1,2,3,4-tetrahydroquinoline-6-carbonitrile (52 mg, 0.3 mmol), prepared as described in Example 1F, in CH2Cl2 (2 mL) at RT was added phenyl isocyanate (33 μl, 0.3 mmol) dropwise. After addition, the reaction was stirred at RT for 1 h. The product was collected by filtration and washed with CH2Cl2-hexanes (1:1) to give the title compound (85 mg, 97%) as a white solid.

Workup

  1. additionAfter addition
  2. filtrationThe product was collected by filtration
  3. washwashed with CH2Cl2-hexanes (1:1)

Sources & evidence

ORD record
ord-04b3c0ce16c34ef4b9184006199c6459
Source dataset
uspto-grants-2010_05
Patent number
US07709647B2

Reaction notes

Loading…