Sodium Cyanate → [4-(3'-Chloro-2-fluoro-6-methoxy-biphenyl-3-ylmethyl)-phenyl]-urea

HRID 1632032Notes

Reaction equation

HRID 1632032 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[C:13]([O:14][CH3:15])=[CH:12][CH:11]=[C:10]([CH2:16][C:17]3[CH:22]=[CH:21][C:20]([NH2:23])=[CH:19][CH:18]=3)[C:9]=2[F:24])[CH:5]=[CH:6][CH:7]=1.[O-:25][C:26]#[N:27].[Na+].CC(C)=O.CCCCCC>CC(O)=O.O>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[C:13]([O:14][CH3:15])=[CH:12][CH:11]=[C:10]([CH2:16][C:17]3[CH:18]=[CH:19][C:20]([NH:23][C:26]([NH2:27])=[O:25])=[CH:21][CH:22]=3)[C:9]=2[F:24])[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 517096Sodium CyanateHCID 21880519Acetone hexaneHCID 580200234-(3'-Chloro-2-fluoro-6-methoxy-biphenyl-3-ylmethyl)-phenylamine

Product 1

HCID 46213059[4-(3'-Chloro-2-fluoro-6-methoxy-biphenyl-3-ylmethyl)-phenyl]-ureaYield 56%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent2×

Procedure

A mixture of 4-(3′-chloro-2-fluoro-6-methoxy-biphenyl-3-ylmethyl)-phenylamine (I-35) (100 mg, 0.26 mmol, 1 eq.), sodium cyanate (74 mg, 0.52 mmol, 2 eq.) in HOAc (1 ml) and water (1 ml) was sonicated at rt for 20 min. then was shaken at rt overnight. The mixture was diluted with water. The precipitate was collected by filtration and washed with water. After dried, 71 mg of crude product containing a less polar by product (presumably the corresponding acetamide) was obtained. Trituration of the crude product with acetone/hexane gave 56 mg of [4-(3′-chloro-2-fluoro-6-methoxy-biphenyl-3-ylmethyl)-phenyl]-urea (P-243) as white solid in 56% yield. 1H NMR (DMSO-d6, 400 MHz): 8.42 (s, 1H), 7.40-7.47 (m, 2H), 7.36 (m, 1H), 7.23-7.32 (m, 4H), 7.07 (m, 2H), 6.92 (m, 1H), 5.76 (s, 2H), 3.83 (s, 2H), 3.72 (s, 3H) ppm.

Workup

  1. customwas sonicated at rt for 20 min.
  2. filtrationThe precipitate was collected by filtration
  3. washwashed with water
  4. customAfter dried
  5. addition71 mg of crude product containing a less polar by product (presumably the corresponding acetamide)
  6. customwas obtained

Sources & evidence

ORD record
ord-b15e265d93554cc1a043e8d2a4f5088b
Source dataset
uspto-grants-2014_07
Patent number
US08791267B2

Reaction notes

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