Mucochloric Acid → HCID 17989685, compound

HRID 1271084Notes

Reaction equation

HRID 1271084 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[N:14]=[C:13]([C:15]3[CH:20]=[CH:19][N:18]=[C:17]([NH:21][NH2:22])[CH:16]=3)[CH:12]=[CH:11][N:10]=2)[CH:5]=[CH:6][CH:7]=1.[C:23](O)(=[O:30])/[C:24](=[C:26](\[CH:28]=O)/[Cl:27])/[Cl:25]>C(O)(=O)C>[Cl:25][C:24]1[C:23](=[O:30])[N:21]([C:17]2[CH:16]=[C:15]([C:13]3[CH:12]=[CH:11][N:10]=[C:9]([NH:8][C:4]4[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=4)[N:14]=3)[CH:20]=[CH:19][N:18]=2)[N:22]=[CH:28][C:26]=1[Cl:27]

Participants

4

Reactant 2

HCID 2771871Mucochloric AcidHCID 21948216HCID 21948216, compound

Product 1

HCID 17989685HCID 17989685, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
125 °C

Procedure

To a suspension of (3-Chloro-phenyl)-[4-(2-hydrazino-pyridin-4-yl)-pyrimidin-2-yl]-amine (5 g) in acetic acid (80 mL) was added 2.8 g of Mucochloric acid. The mixture was heated at 125° C. for 4 h. The solvent was concentrated and the crude was poured into water (500 mL). The suspension was neutralised by addition of solid potassium carbonate until pH 7. The aqueous phase was extracted with ethyl acetate (3×200 mL). The organic phases were combined, dried over MgSO4, and concentrated. Flash silica chromatography, eluting with ethyl acetate-tetrahydrofuran (1-0 to 1-1), afforded the title compound as a solid (3.11 g, 44%). Mp 238–240° C., 1H NMR (DMSO-d6) 10.3 (1H, s, NH), 8.84 (1H, d, 5 Hz), 8.76 (1H, d, 5 Hz), 8.42 (1H, s), 8.38 (1H, s), 8.28 (1H, 2 Hz, 5 Hz), 8.04 (1H, t, 2 Hz), 7.74 (1H, dd), 7.62 (1H, d, 5 Hz), 7.32 (1H, t, 8 Hz), 7.02 (1H, dd, 2 Hz, 8 Hz). 13CNMR DMSO-d6) 160.3, 160.2, 159.9, 155.5, 153.5, 150.2, 146.6, 141.7, 136.7, 136.6, 134.0, 132.9, 130.1, 121.9, 121.1, 118.7, 118.2, 117.3, 109.3.

Workup

  1. concentrationThe solvent was concentrated
  2. additionthe crude was poured into water (500 mL)
  3. additionThe suspension was neutralised by addition of solid potassium carbonate until pH 7
  4. extractionThe aqueous phase was extracted with ethyl acetate (3×200 mL)
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated
  7. washFlash silica chromatography, eluting with ethyl acetate-tetrahydrofuran (1-0 to 1-1)

Sources & evidence

ORD record
ord-90c0ec26f9e54b30bb97098750757dc9
Source dataset
uspto-grants-2007_04
Patent number
US07205301B2

Reaction notes

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