Acetic Acid → HCID 58020315, compound

HRID 1632043Notes

Reaction equation

HRID 1632043 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[CH:10]=[CH:11][C:12]([O:24][CH3:25])=[C:13]([C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([C:21](=[O:23])[CH3:22])[CH:16]=3)[CH:14]=2)=[CH:4][CH:3]=1.C(O)(=O)C.[O-:30][C:31]#[N:32].[Na+]>O>[C:21]([C:17]1[CH:16]=[C:15]([C:13]2[C:12]([O:24][CH3:25])=[CH:11][CH:10]=[C:9]([NH:8][C:5]3[CH:4]=[CH:3][C:2]([NH:1][C:31]([NH2:32])=[O:30])=[CH:7][CH:6]=3)[CH:14]=2)[CH:20]=[CH:19][CH:18]=1)(=[O:23])[CH3:22]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 517096Sodium CyanateHCID 58020021HCID 58020021, compound

Product 1

HCID 58020315HCID 58020315, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

In an 8 mL vial equipped with a stir bar was placed 1-[5′-(4-amino-phenylamino)-2′-methoxy-biphenyl-3-yl]-ethanone synthesized above (free base) (60.0 mg, 0.180 mmol), water (600 μL), acetic acid (300 μL) and sodium cyanate (46.8 mg, 0.720 mmol). The mixture was stirred at room temperature for 4 hours and then water (20 mL) was added followed by an P-traction with (2×30 mL). The organic portions were combined, washed with brine (30 mL), dried (MgSO4) and concentrated. The crude material was purified by column utilizing 75% acetone/DCM as the eluent to produce 32 mg of [4-(3′-acetyl-6-methoxy-biphenyl-3-ylamino)-phenyl]-urea (P-268) as a light brown solid in 47% yield. MS (APCI+): 376.1 (M+1); LC-MS: 94%.

Workup

  1. customIn an 8 mL vial equipped with a stir bar
  2. washwashed with brine (30 mL)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. customThe crude material was purified by column

Sources & evidence

ORD record
ord-202ecd7491854d339d892c358b4a2678
Source dataset
uspto-grants-2014_07
Patent number
US08791267B2

Reaction notes

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