Ethylenediamine → HCID 71288437, compound

HRID 246207Notes

Reaction equation

HRID 246207 reaction equation
[OH:1][CH2:2][C@H:3]([NH:5][C:6]([C:8]1[C:16]2[C:11](=[N:12][CH:13]=[C:14]([C:17]3[C:25]4[C:20](=[CH:21][C:22]([Cl:26])=[CH:23][CH:24]=4)[N:19]([CH3:27])[N:18]=3)[N:15]=2)[N:10](COCC[Si](C)(C)C)[CH:9]=1)=[O:7])[CH3:4].C(Cl)Cl.C(N)CN>C(O)(C(F)(F)F)=O>[OH:1][CH2:2][C@H:3]([NH:5][C:6]([C:8]1[C:16]2[C:11](=[N:12][CH:13]=[C:14]([C:17]3[C:25]4[C:20](=[CH:21][C:22]([Cl:26])=[CH:23][CH:24]=4)[N:19]([CH3:27])[N:18]=3)[N:15]=2)[NH:10][CH:9]=1)=[O:7])[CH3:4]

Participants

5

Reactant 3

HCID 3301EthylenediamineHCID 6344DichloromethaneHCID 712860912-(6-chloro-1-methyl-1H-indazol-3-yl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid ((R)-2-hydroxy-1-methyl-ethyl)-amide

Product 1

HCID 71288437HCID 71288437, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

2-(6-Chloro-1-methyl-1H-indazol-3-yl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid ((R)-2-hydroxy-1-methyl-ethyl)-amide (35 mg, 0.068 mol) was dissolved in a 4:6 solution of TFA:DCM (10 mL). After stirring at room temperature overnight, the volatiles were removed under reduced pressure. The crude material was then dissolved in dichloromethane and treated with ethylenediamine (41 mg, 0.68 mmol). After stirring at room temperature overnight, the precipitate was collected by filtration to afford 15 mg (57%) of 2-(6-chloro-1-methyl-1H-indazol-3-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid ((R)-2-hydroxy-1-methyl-ethyl)-amide as a yellow solid. MS: (M+H)+=385; 1H NMR (300 MHz, DMSO-d6) δ ppm 8.97 (d, J=2.64 Hz, 1H) 8.66 (d, J=8.69 Hz, 1H) 8.36 (s, 1H) 8.15 (d, J=7.93 Hz, 1H) 7.92 (s, 1H) 7.26 (d, J=8.31 Hz, 1H) 3.96-4.39 (m, 3H) 3.31-3.68 (m, 1H) 1.25 (d, J=6.80 Hz, 3H).

Workup

  1. customthe volatiles were removed under reduced pressure
  2. dissolutionThe crude material was then dissolved in dichloromethane
  3. stirringAfter stirring at room temperature overnight
  4. filtrationthe precipitate was collected by filtration

Sources & evidence

ORD record
ord-b088a429c3f247e486eeeedc0a0dad9c
Source dataset
uspto-grants-2014_02
Patent number
US08658646B2

Reaction notes

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