Hydrazine hydrate (1:1) → HCID 86732071, compound

HRID 1498811Notes

Reaction equation

HRID 1498811 reaction equation
Cl[C:2]1[N:7]=[C:6]([CH3:8])[N:5]=[C:4]([C@@H:9]2[CH2:11][C@H:10]2[C:12]2[N:16]([CH3:17])[C:15]3[CH:18]=[CH:19][CH:20]=[CH:21][C:14]=3[N:13]=2)[CH:3]=1.O.[NH2:23][NH2:24]>O1CCCC1>[NH:23]([C:2]1[N:7]=[C:6]([CH3:8])[N:5]=[C:4]([C@@H:9]2[CH2:11][C@H:10]2[C:12]2[N:16]([CH3:17])[C:15]3[CH:18]=[CH:19][CH:20]=[CH:21][C:14]=3[N:13]=2)[CH:3]=1)[NH2:24]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 86732072HCID 86732072, compound

Product 1

HCID 86732071HCID 86732071, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-((1R,2R)-2-(6-chloro-2-methylpyrimidin-4-yl)cyclopropyl)-1-methyl-1H-benzo[d]imidazole (4-6, 200 mg, 0.0.669 mmol, 1.0 eq) and hydrazine hydrate (335 mg, 6.69 mmol, 10 eq) in tetrahydrofuran (3 mL) was heated by microwave irradiation at 80° C. for 40 minutes. The reaction mixture was filtered and concentrated to dryness. The afford 2-((1R,2R)-2-(6-hydrazinyl-2-methylpyrimidin-4-yl)cyclopropyl)-1-methyl-1H-benzo[d]imidazole (4-7) as a glassy yellow solid. LRMS m/z (M+H) 294.4 found, 294.2 required.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-756a96e6875145639f025cb4a26dc811
Source dataset
uspto-grants-2015_12
Patent number
US09200001B2

Reaction notes

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