Ammonium Chloride → HCID 67252895, compound

HRID 1711712Notes

Reaction equation

HRID 1711712 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-7a6b9f1d7827435e8f49267cac58c4df
Source dataset
uspto-grants-2010_09
Patent number
US07790756B2

Reaction notes

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