Hydrochloric Acid → HCID 178481258, compound

HRID 1921675Notes

Reaction equation

HRID 1921675 reaction equation
[CH3:1][C:2]([NH:34]C(=O)OC(C)(C)C)([C:4]1[CH:9]=[CH:8][C:7]([C:10]([NH:21][C:22]2[CH:27]=[CH:26][C:25]([C:28]3[N:29]=[CH:30][N:31]([CH3:33])[CH:32]=3)=[CH:24][CH:23]=2)=[C:11]2[C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=3[O:13][C:12]2=[O:20])=[CH:6][CH:5]=1)[CH3:3].Cl>O1CCOCC1>[NH2:34][C:2]([C:4]1[CH:9]=[CH:8][C:7]([C:10]([NH:21][C:22]2[CH:27]=[CH:26][C:25]([C:28]3[N:29]=[CH:30][N:31]([CH3:33])[CH:32]=3)=[CH:24][CH:23]=2)=[C:11]2[C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=3[O:13][C:12]2=[O:20])=[CH:6][CH:5]=1)([CH3:3])[CH3:1]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 178481260HCID 178481260, compound

Product 1

HCID 178481258HCID 178481258, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

2.5 g of tert-butyl (1-methyl-1-{4-[[4-(1-methyl-1H-imidazol-4-yl)phenylamino]-(2-oxobenzofuran-3-ylidene)methyl]phenyl}ethyl)carbamate (N-Boc derivative of Example 56) was dissolved in 50 mL of dioxane and combined with 50 mL of a 4N solution of hydrogen chloride in dioxane. The solution was stirred for 1 hour at RT and evaporated down. The residue was dissolved in 50 mL of methanol and evaporated down with another 150 mL of isopropanol almost to the residue and then crystallized. After diluting with acetone, the product was suction filtered and washed with acetone. Yield: 1.9 g of yellow crystals of melting point>280° C. as hydrochloride; Rf value: 0.18 (dichloromethane/methanol (8:2)).

Workup

  1. customevaporated down
  2. dissolutionThe residue was dissolved in 50 mL of methanol
  3. customevaporated down with another 150 mL of isopropanol almost to the residue
  4. customcrystallized
  5. additionAfter diluting with acetone
  6. filtrationfiltered
  7. washwashed with acetone

Sources & evidence

ORD record
ord-7b016cfb53934e61b73cf2a598c9463e
Source dataset
uspto-grants-2012_05
Patent number
US08173699B2

Reaction notes

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