Hydrochloric Acid → HCID 178483337, compound

HRID 1353931Notes

Reaction equation

HRID 1353931 reaction equation
C(O[N:4]=[CH:5][C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[NH:11][N:10]=[C:9]2[C:15]1[CH:16]=[C:17]([C:21]([NH:23][C:24]2[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=2)=[O:22])[CH:18]=[CH:19][CH:20]=1)C.[NH2:31][NH:32][C:33](=O)[CH2:34][N:35]([CH3:37])[CH3:36].C[O-].[Na+].Cl>CO.C(OCC)(=O)C>[CH3:36][N:35]([CH2:34][C:33]1[N:4]=[C:5]([C:6]2[CH:7]=[C:8]3[C:12](=[CH:13][CH:14]=2)[NH:11][N:10]=[C:9]3[C:15]2[CH:16]=[C:17]([C:21]([NH:23][C:24]3[CH:25]=[CH:26][C:27]([F:30])=[CH:28][CH:29]=3)=[O:22])[CH:18]=[CH:19][CH:20]=2)[NH:31][N:32]=1)[CH3:37]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 683192-(Dimethylamino)acetohydrazideHCID 10942334Sodium MethoxideHCID 131724926HCID 131724926, compound

Product 1

HCID 178483337HCID 178483337, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent3×HCID 8857Ethyl AcetateSolvent

Procedure

Prepared according to the procedure of Example 367 C using (3-[5-(ethoxyiminomethyl)(1H-indazol-3-yl)]phenyl)-N-(4-fluorophenyl)carboxamide.2HCl (1.50 g, 3.15 mmol), N-amino-2-(dimethylamino) acetamide (1.2 g, 10.33 mmol) and sodium methoxide (1.8 mL of a 25% w/w in methanol) in anhydrous methanol (20.0 mL) with a reaction time of 1.5 days. Purification by flash chromatography on silica gel using 50% methanol in ethyl acetate afforded a solid which was dissolved in anhydrous methanol and treated with anhydrous hydrogen chloride gas for 10 min at 0° C. After stirring at ambient temperature for 5 min anhydrous ethyl acetate was added to precipitate the desired product which was collected on a sintered glass funnel, washed with methanol and ethyl acetate and dried under vacuum to give the title compound (267 mg, 50% yield) as a light yellow solid 1H NMR (DMSO-d6) δ 13.5 (br s, 1H), 10.5 (s, 1H), 8.5 (s, 1H), 8.2 (br d, 1H), 8.1 (d, 1H), 8.0 (d, 1H), 7.84 (dd, 2H), 7.75–7.6 (m, 2H), 7.2 (t, 2H), 3.6 (bs, 2H), 2.2 (s, 6H), ES-MS (m/z) 456 [M+H]+.

Workup

  1. customPrepared
  2. customwith a reaction time of 1.5 days
  3. customPurification by flash chromatography on silica gel using 50% methanol in ethyl acetate
  4. customafforded a solid which
  5. additionwas added
  6. customto precipitate the desired product which
  7. customwas collected on a sintered glass funnel
  8. washwashed with methanol and ethyl acetate
  9. customdried under vacuum

Sources & evidence

ORD record
ord-f98be4a3d8464f1ea8f6db48edb1993b
Source dataset
uspto-grants-2007_05
Patent number
US07220771B2

Reaction notes

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