Ethylenediamine → 2-Hydroxy-1,1-dimethyl-ethyl-amide

HRID 246561

Reaction equation

HRID 246561 reaction equation
[F:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:12]3[N:13]=[C:14]4[C:20]([C:21]([NH:23][C:24]([CH3:28])([CH3:27])[CH2:25][OH:26])=[O:22])=[CH:19][N:18](COCC[Si](C)(C)C)[C:15]4=[N:16][CH:17]=3)=[N:7][N:8]2[CH3:11])=[CH:4][CH:3]=1.FC(F)(F)C(O)=[O:40].C(N)CN>ClCCl>[F:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:12]3[N:13]=[C:14]4[C:20]([C:21]([OH:40])=[O:22])=[CH:19][NH:18][C:15]4=[N:16][CH:17]=3)=[N:7][N:8]2[CH3:11])=[CH:4][CH:3]=1.[OH:26][CH2:25][C:24]([NH-:23])([CH3:28])[CH3:27]

Participants

6

Reactant 3

HCID 3301EthylenediamineHCID 6422Trifluoroacetic acidHCID 712804242-(6-Fluoro-1-methyl-1H-indazol-3-yl)-N-(1-hydroxy-2-methylpropan-2-yl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide

Product 2

HCID 712796392-(6-fluoro-1-methyl-1H-indazol-3-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acidHCID 866779892-Hydroxy-1,1-dimethyl-ethyl-amideYield 174.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

2-(6-Fluoro-1-methyl-1H-indazol-3-yl)-N-(1-hydroxy-2-methylpropan-2-yl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (0.08 g, 0.156 mmol), and trifluoroacetic acid (1 mL, 13.0 mmol) were stirred in dichloromethane for 15 h. The reaction mixture was concentrated in vacuo then ethylenediamine (1 mL, 14.8 mmol) in dichloromethane (5 mL) was added. After 1 h, the mixture was concentrated to dryness and water (1 mL) added. The solid precipitate was collected by filtration and dried to give 2-(6-fluoro-1-methyl-1H-indazol-3-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (2-hydroxy-1,1-dimethyl-ethyl-amide (24 mg, 36%). MS (M+H)+=383; 1H NMR (DMSO-d6) δ: 9.07 (s, 1H), 8.60 (dd, J=8.7, 5.5 Hz, 1H), 8.37 (s, 1H), 7.91 (s, 1H), 7.66 (d, J=9.8 Hz, 1H), 7.15 (t, J=8.3 Hz, 1H), 4.14 (s, 3H), 3.62 (s, 2H), 1.45 (s, 6H).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. concentrationthe mixture was concentrated to dryness and water (1 mL)
  3. additionadded
  4. filtrationThe solid precipitate was collected by filtration
  5. customdried

Sources & evidence

ORD record
ord-7cd1dc268fce4e0eb78b95b2101fbd68
Source dataset
uspto-grants-2014_02
Patent number
US08658646B2

Linked notes

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