Hydrazine → HCID 86678995, compound

HRID 2203360Notes

Reaction equation

HRID 2203360 reaction equation
[NH2:1][NH2:2].[NH2:3][C:4]1[C:5]2[C:30]([CH3:36])([C:31]([O:33]CC)=O)[C:29](=[O:37])[NH:28][C:6]=2[N:7]=[C:8]([C:10]2[C:18]3[C:13](=[N:14][CH:15]=[CH:16][CH:17]=3)[N:12]([CH2:19][CH2:20][C:21]([F:27])([F:26])[C:22]([F:25])([F:24])[F:23])[N:11]=2)[N:9]=1>>[NH2:3][C:4]1[C:5]2[C:30]([CH3:36])([C:31]([NH:1][NH2:2])=[O:33])[C:29](=[O:37])[NH:28][C:6]=2[N:7]=[C:8]([C:10]2[C:18]3[C:13](=[N:14][CH:15]=[CH:16][CH:17]=3)[N:12]([CH2:19][CH2:20][C:21]([F:27])([F:26])[C:22]([F:24])([F:23])[F:25])[N:11]=2)[N:9]=1

Participants

3

Reactant 2

HCID 9321HydrazineHCID 86678987HCID 86678987, compound

Product 1

HCID 86678995HCID 86678995, compound

Conditions

Temperature
80 °C

Procedure

Hydrazine (2 mL, 63.7 mmol) was added to ethyl 4-amino-5-methyl-6-oxo-2-[1-(3,3,4,4,4-pentafluorobutyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidine-5-carboxylate, as prepared by the procedure described in Example 158, (400 mg, 0.761 mmol) and the reaction mixture was heated to 80° C. for 30 min. The reaction was then cooled to room temperature and concentrated in vacuo. Excess hydrazine was azeotropically removed by treatment with acetonitrile (3×4 mL). The product was lyophilized from water/acetonitrile overnight to give the title compound as a pale yellow solid which was used in the next step without further purification. m/z=486.01 (M+H).

Workup

  1. customas prepared by the procedure
  2. temperatureThe reaction was then cooled to room temperature
  3. concentrationconcentrated in vacuo
  4. customExcess hydrazine was azeotropically removed by treatment with acetonitrile (3×4 mL)
  5. customwas lyophilized from water/acetonitrile overnight

Sources & evidence

ORD record
ord-4193df4e964a404e842f927cdff32ab3
Source dataset
uspto-grants-2016_06
Patent number
US09365574B2

Reaction notes

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