Ammonium Chloride → HCID 67252895, compound

HRID 2042132Notes

Reaction equation

HRID 2042132 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]2[CH:10]=[N:11][C:12]([N+:15]([O-])=O)=[CH:13][CH:14]=2)=[CH:4][C:3]=1[NH:18][C:19]([NH:21][C:22]1[N:26]([C:27]2[CH:28]=[C:29]3[C:34](=[CH:35][CH:36]=2)[N:33]=[CH:32][CH:31]=[CH:30]3)[N:25]=[C:24]([CH:37]([CH3:39])[CH3:38])[CH:23]=1)=[O:20].[NH4+].[Cl-]>CO.[Zn]>[NH2:15][C:12]1[N:11]=[CH:10][C:9]([O:8][C:5]2[CH:6]=[CH:7][C:2]([F:1])=[C:3]([NH:18][C:19]([NH:21][C:22]3[N:26]([C:27]4[CH:28]=[C:29]5[C:34](=[CH:35][CH:36]=4)[N:33]=[CH:32][CH:31]=[CH:30]5)[N:25]=[C:24]([CH:37]([CH3:38])[CH3:39])[CH:23]=3)=[O:20])[CH:4]=2)=[CH:14][CH:13]=1

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 67254230HCID 67254230, compound

Product 1

HCID 67252895HCID 67252895, compoundYield 41%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 887MethanolSolvent

Procedure

1-(2-fluoro-5-(6-nitropyridin-3-yloxy)phenyl)-3-(3-isopropyl-1-(quinolin-6-yl)-1H-pyrazol-5-yl)urea (0.129 g, 0.245 mmol) was dissolved in MeOH (2.0 mL), to which NH4Cl (0.131 g, 2.45 mmol) and zinc power (0.160 g, 2.45 mmol) were added and the reaction mixture was stirred at RT for 4 h. The reaction mixture was filtered through Celite and washed with methanol (30 mL) and EtOAc (50 mL). The filtrate was concentrated in vacuum, partitioned between EtOAc (30 mL) and water (20 mL). The separated organic phase was washed with brine (10 mL), dried (MgSO4) and concentrated to afford 1-(5-(6-aminopyridin-3-yloxy)-2-fluorophenyl)-3-(3-isopropyl-1-(quinolin-6-yl)-1H-pyrazol-5-yl)urea (0.0495 g, 41% yield) as a white foam. MS (ESI) m/z: 498.2 (M+H+).

Workup

  1. additionwere added
  2. filtrationThe reaction mixture was filtered through Celite
  3. washwashed with methanol (30 mL) and EtOAc (50 mL)
  4. concentrationThe filtrate was concentrated in vacuum
  5. custompartitioned between EtOAc (30 mL) and water (20 mL)
  6. washThe separated organic phase was washed with brine (10 mL)
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-64972e969a534aec984debe210891db1
Source dataset
uspto-grants-2013_11
Patent number
US08586565B2

Reaction notes

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