1,2-Dichloroethane → HCID 86732534, compound

HRID 1777009Notes

Reaction equation

HRID 1777009 reaction equation
C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].O=[C:16]1[CH2:24][CH2:23][C:22]2[C:18](=[CH:19][N:20]([C:25]([O:27][CH2:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)=[O:26])[N:21]=2)[CH2:17]1.[CH:35]1([NH2:38])[CH2:37][CH2:36]1.C(=O)(O)[O-].[Cl:43]CCCl>O.C(O)(=O)C>[ClH:43].[CH:35]1([NH:38][CH:16]2[CH2:24][CH2:23][C:22]3[C:18](=[CH:19][N:20]([C:25]([O:27][CH2:28][C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)=[O:26])[N:21]=3)[CH2:17]2)[CH2:37][CH2:36]1

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 769Bicarbonate IonHCID 69828CyclopropylamineHCID 5049666Sodium triacetoxyborohydrideHCID 86732536HCID 86732536, compound

Product 1

HCID 86732534HCID 86732534, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

Sodium triacetoxy borohydride (5.41 g) and acetic acid (2.19 mL) were added to a mixture of a mixture (3.45 g) of benzyl 5-oxo-4,5,6,7-tetrahydro-2H-indazole-2-carboxylate and a regioisomer thereof, cyclopropylamine (0.878 mL), and 1,2-dichloroethane (70 mL) under an argon gas atmosphere, followed by stirring for 18 hours at room temperature. Water was added to the reaction liquid, followed by stirring for 2 hours at room temperature, and then pH thereof was adjusted to 8 by using saturated aqueous bicarbonate, followed by liquid separation. The organic layer was dried and then concentrated under reduced pressure. A dioxane solution (4.15 mL) of 4 M hydrogen chloride was added to a mixture of the residue and ethyl acetate (100 mL), followed by stirring for an hour at room temperature. The precipitate was collected by filtration and washed with ethyl acetate, thereby obtaining a mixture (3.26 g) of benzyl 5-(cyclopropylamino)-4,5,6,7-tetrahydro-2H-indazole-2-carboxylate monohydrochloride and a regioisomer thereof.

Workup

  1. stirringby stirring for 2 hours at room temperature
  2. customfollowed by liquid separation
  3. customThe organic layer was dried
  4. concentrationconcentrated under reduced pressure
  5. additionA dioxane solution (4.15 mL) of 4 M hydrogen chloride was added to a mixture of the residue and ethyl acetate (100 mL)
  6. stirringby stirring for an hour at room temperature
  7. filtrationThe precipitate was collected by filtration
  8. washwashed with ethyl acetate

Sources & evidence

ORD record
ord-ba22d8623c4b46c688a67c4af1214d14
Source dataset
uspto-grants-2016_02
Patent number
US09266840B2

Reaction notes

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