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Ammonium Chloride → HCID 86677241, compound

HRID 1842714
Notes
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Reaction equation

HRID 1842714 reaction equation
[Cl:1][C:2]1[C:3]([C:27]2[CH:28]=[N:29][N:30]3[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=23)=[N:4][C:5]([NH:8][C:9]2[CH:14]=[C:13]([N+:15]([O-])=O)[C:12]([C:18]3[CH2:19][CH2:20][N:21]([CH3:24])[CH2:22][CH:23]=3)=[CH:11][C:10]=2[O:25][CH3:26])=[N:6][CH:7]=1.[NH4+].[Cl-]>C(O)C.O.[Fe]>[Cl:1][C:2]1[C:3]([C:27]2[CH:28]=[N:29][N:30]3[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=23)=[N:4][C:5]([NH:8][C:9]2[CH:14]=[C:13]([NH2:15])[C:12]([C:18]3[CH2:19][CH2:20][N:21]([CH3:24])[CH2:22][CH:23]=3)=[CH:11][C:10]=2[O:25][CH3:26])=[N:6][CH:7]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 71240866HCID 71240866, compound2×

Product 1

HCID 86677241HCID 86677241, compoundYield 88%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolvent
HCID 962
Water
Solvent

Procedure

A mixture of 5-chloro-N-[2-methoxy-4-(1-methyl-3,6-dihydro-2H-pyridin-4-yl)-5-nitrophenyl]-4-pyrazolo[1,5-a]pyridin-3-ylpyrimidin-2-amine (Intermediate 56, 470 mg, 0.96 mmol), iron (320 mg, 5.73 mmol) and NH4Cl (35.8 mg, 0.67 mmol) in ethanol (19 mL) and water (6.33 mL) was heated at reflux for 4 h. Then the mixture was cooled and concentrated in vacuo to give a thick slurry which was triturated with 10% CH3OH in CH2Cl2 (50 mL) for 15 minutes. The mixture was then filtered and a small amount of sat. NaHCO3 was added to the filtrate. The resulting phases were separated and the aqueous solution was extracted with 10% CH3OH in CH2Cl2 (50 mL). The combined organic solutions were washed with brine, dried (Na2SO4) and concentrated in vacuo. Purification by FCC, eluting with 2.5% 7N methanolic ammonia in CH2Cl2 gave the title compound (387 mg, 88%) as a yellow foam; 1H NMR: 2.31 (3H, s), 2.38-2.44 (2H, m), 2.61 (2H, t), 3.02 (2H, dd), 3.68 (3H, s), 4.33 (2H, d), 5.72-5.76 (1H, m), 6.66 (1H, s), 7.08 (1H, s), 7.14 (1H, td), 7.35-7.43 (1H, m), 8.41 (1H, s), 8.44 (1H, s), 8.49 (1H, d), 8.84 (1H, d), 8.96 (1H, s); m/z: ES+ MH+ 462.5.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 4 h
  3. temperatureThen the mixture was cooled
  4. concentrationconcentrated in vacuo
  5. customto give a thick slurry which
  6. customwas triturated with 10% CH3OH in CH2Cl2 (50 mL) for 15 minutes
  7. filtrationThe mixture was then filtered
  8. additiona small amount of sat. NaHCO3 was added to the filtrate
  9. customThe resulting phases were separated
  10. extractionthe aqueous solution was extracted with 10% CH3OH in CH2Cl2 (50 mL)
  11. washThe combined organic solutions were washed with brine
  12. dry with materialdried (Na2SO4)
  13. concentrationconcentrated in vacuo
  14. customPurification by FCC
  15. washeluting with 2.5% 7N methanolic ammonia in CH2Cl2

Sources & evidence

ORD record
ord-e55c05ca265949fbbff1dfb964837b79
Source dataset
uspto-grants-2015_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08946235B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes