Diisopropylethylamine → HCID 57585767, compound

HRID 645718Notes

Reaction equation

HRID 645718 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]=[CH:30][CH:29]=[C:28]2[C:24]=1[CH:25]=[N:26][NH:27]2.CCN(C(C)C)C(C)C>C(O)CCC.CCOC(C)=O>[Cl:1][C:2]1[N:3]=[C:4]([NH:22][C:23]2[CH:31]=[CH:30][CH:29]=[C:28]3[C:24]=2[CH:25]=[N:26][NH:27]3)[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

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 413085NoName_3327HCID 534868282,4-dichloro-7-tosyl-7H-pyrrolo[2,3-d]pyrimidine

Product 1

HCID 57585767HCID 57585767, compoundYield 93.4%

Reagents, catalysts & solvents 2

HCID 2631-ButanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 2,4-dichloro-7-tosyl-pyrrolo[2,3-d]pyrimidine (0.68 g, 2 mmol) in nBuOH (5 ml) was added 4-aminoindazole (0.293 g, 2.2 mmol) and DIPEA (0.534 mL, 3 mmol) at room temperature. After heating at 90° C. for 15 h, it was diluted with EtOAc, the organic layer was washed with 1N HCl, Sat NaHCO3, brine, dried and concentrated to give crude 2-chloro-N-(1H-indazol-4-yl)-7-tosyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine (0.82 g).

Workup

  1. washthe organic layer was washed with 1N HCl, Sat NaHCO3, brine
  2. customdried
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-aeaa5b48cac64e3f9b52e8b8b3dc8298
Source dataset
uspto-grants-2010_04
Patent number
US07705004B2

Reaction notes

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