1H-Indazol-6-amine → HCID 57585784, compound

HRID 645699Notes

Reaction equation

HRID 645699 reaction equation
[Cl:1][C:2]1[N:3]=[C:4](Cl)[C:5]2[CH:10]=[CH:9][N:8]([S:11]([C:14]3[CH:20]=[CH:19][C:17]([CH3:18])=[CH:16][CH:15]=3)(=[O:13])=[O:12])[C:6]=2[N:7]=1.[NH2:22][C:23]1[CH:31]=[C:30]2[C:26](C=N[NH:29]2)=[CH:25][CH:24]=1.C[CH2:33][N:34](C(C)C)C(C)C>C(O)CCC.C(OCC)(=O)C>[NH:29]1[C:30]2[CH:31]=[C:23]([NH:22][C:4]3[C:5]4[CH:10]=[CH:9][N:8]([S:11]([C:14]5[CH:20]=[CH:19][C:17]([CH3:18])=[CH:16][CH:15]=5)(=[O:13])=[O:12])[C:6]=4[N:7]=[C:2]([Cl:1])[N:3]=3)[CH:24]=[CH:25][C:26]=2[N:34]=[CH:33]1

Participants

6

Reactant 3

HCID 814231H-Indazol-6-amineHCID 81531DiisopropylethylamineHCID 534868282,4-dichloro-7-tosyl-7H-pyrrolo[2,3-d]pyrimidine

Product 1

HCID 57585784HCID 57585784, compoundYield 85.4%

Reagents, catalysts & solvents 2

HCID 2631-ButanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 2,4-dichloro-7-tosyl-pyrrolo[2,3-d]pyrimidine (0.1 g, 0.28 mmol) in n-butyl alcohol (1 mL) was added 6-aminoindazole (0.043 g, 0.32 mmol) and DIPEA (0.057 mL, 0.32 mmol) at room temperature. After heating at 80° C. for 15 h, the mixture was diluted with ethyl acetate, and the organic layer was sequentially washed with 1N HCl, Sat NaHCO3, and brine. The organic extract was dried over Na2SO4 and concentrated to give crude N-(1H-benzo[d]imidazol-6-yl)-2-chloro-7-tosyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine (0.105 g).

Workup

  1. washthe organic layer was sequentially washed with 1N HCl, Sat NaHCO3, and brine
  2. extractionThe organic extract
  3. dry with materialwas dried over Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-0b26902566f94e0abf1be91498027764
Source dataset
uspto-grants-2010_04
Patent number
US07705004B2

Reaction notes

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