Triethylamine → HCID 25195903, compound

HRID 645685Notes

Reaction equation

HRID 645685 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([NH:10][C:11]3[C:12]4[CH:32]=[CH:31][NH:30][C:13]=4[N:14]=[C:15]([NH:17][C:18]4[CH:23]=[CH:22][C:21]([N:24]5[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]5)=[CH:20][CH:19]=4)[N:16]=3)[CH:8]=2)[CH:3]=[N:2]1.C(N(CC)CC)C.[CH3:40][S:41](Cl)(=[O:43])=[O:42]>C(Cl)Cl>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([NH:10][C:11]3[C:12]4[CH:32]=[CH:31][NH:30][C:13]=4[N:14]=[C:15]([NH:17][C:18]4[CH:23]=[CH:22][C:21]([N:24]5[CH2:25][CH2:26][N:27]([S:41]([CH3:40])(=[O:43])=[O:42])[CH2:28][CH2:29]5)=[CH:20][CH:19]=4)[N:16]=3)[CH:8]=2)[CH:3]=[N:2]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 25195690HCID 25195690, compound

Product 1

HCID 25195903HCID 25195903, compoundYield 18.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of N4-(1H-indazol-6-yl)-N2-(4-(piperazin-1-yl)phenyl)-7H-pyrrolo[2,3-d]pyrimidine-2,4-diamine (9 mg, 0.021 mmol) and triethylamine (TEA) (0.010 mL, 0.072 mmol) in CH2Cl2 (1 mL) at room temperature, methanesulfonyl chloride (MeSO2Cl) (0.006 mL, 0.077 mmol) was added. After being stirred at room temperature for 3 h, the mixture was concentrated in vacuo. The residue was purified by HPLC to give N4-(1H-indazol-6-yl)-N2-(4-(4-(methylsulfonyl)piperazin-1-yl)phenyl)-7H-pyrrolo[2,3-d]pyrimidine-2,4-diamine (2 mg), MS 504.3 (M+H) (Compound 8-1); and N4-(1-(methylsulfonyl)-1H-indazol-6-yl)-N2-(4-(4-(methylsulfonyl)piperazin-1-yl)phenyl)-7H-pyrrolo[2,3-d]pyrimidine-2,4-diamine (1 mg), MS 582.4 (M+H) (Compound 8-2).

Workup

  1. concentrationthe mixture was concentrated in vacuo
  2. customThe residue was purified by HPLC

Sources & evidence

ORD record
ord-7942d3997fdf484da4826c0522d40707
Source dataset
uspto-grants-2010_04
Patent number
US07705004B2

Reaction notes

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