Ethylenediamine → HCID 71288456, compound

HRID 246563Notes

Reaction equation

HRID 246563 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:12]3[N:17]=[C:16]4[C:18]([C:29]([NH:31][C:32]([CH3:36])([CH3:35])[CH2:33][OH:34])=[O:30])=[CH:19][N:20](COCC[Si](C)(C)C)[C:15]4=[N:14][CH:13]=3)=[N:7][N:8]2[CH3:11])=[CH:4][CH:3]=1.FC(F)(F)C(O)=O.C(N)CN>ClCCl>[OH:34][CH2:33][C:32]([NH:31][C:29]([C:18]1[C:16]2[C:15](=[N:14][CH:13]=[C:12]([C:6]3[C:5]4[C:9](=[CH:10][C:2]([Cl:1])=[CH:3][CH:4]=4)[N:8]([CH3:11])[N:7]=3)[N:17]=2)[NH:20][CH:19]=1)=[O:30])([CH3:36])[CH3:35]

Participants

5

Reactant 3

HCID 3301EthylenediamineHCID 6422Trifluoroacetic acidHCID 71280063HCID 71280063, compound

Product 1

HCID 71288456HCID 71288456, compoundYield 16.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-(6-Chloro-1-methyl-1H-indazol-3-yl)-N-(1-hydroxy-2-methylpropan-2-yl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[3,2-b]pyrazine-7-carboxamide (0.04 g, 0.076 mmol), trifluoroacetic acid (0.582 mL, 7.56 mmol) and dichloromethane (3.00 mL) were combined and stirred for 3 h. The reaction mixture was concentrated to dryness and diluted with dichloromethane (3 mL), then ethylenediamine (0.510 mL, 7.56 mmol) was added. After 1 h the mixture was concentrated to dryness and ice water (1 mL) added. The solid formed was collected by filtration then triturated with ethyl acetate to obtain 2-(6-chloro-1-methyl-1H-indazol-3-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (2-hydroxy-1,1-dimethyl-ethyl)-amide (5 mg, 16%). MS (M+H)+=399; 1H NMR (DMSO-d6) δ: 8.94-9.36 (m, 1H), 8.51-8.76 (m, 1H), 8.37 (s, 1H), 7.80-8.08 (m, 2H), 7.29 (t, J=8.8 Hz, 1H), 4.17 (d, J=5.8 Hz, 3H), 3.48-3.80 (m, 2H), 1.45 (d, J=3.3 Hz, 6H).

Workup

  1. concentrationThe reaction mixture was concentrated to dryness
  2. additiondiluted with dichloromethane (3 mL)
  3. concentrationAfter 1 h the mixture was concentrated to dryness and ice water (1 mL)
  4. additionadded
  5. customThe solid formed
  6. filtrationwas collected by filtration
  7. customthen triturated with ethyl acetate

Sources & evidence

ORD record
ord-bc3a08c2bde341a4981f473feca60f8b
Source dataset
uspto-grants-2014_02
Patent number
US08658646B2

Reaction notes

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