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Acetic Acid → HCID 58010206, compound

HRID 2204615
Notes
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Reaction equation

HRID 2204615 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH3:12])[CH:7]=[C:6]2[C:13]1[N:23]([CH2:24][O:25][CH2:26][CH2:27][Si:28]([CH3:31])([CH3:30])[CH3:29])[C:16]2=[N:17][CH:18]=[C:19]([CH2:21][NH2:22])[N:20]=[C:15]2[CH:14]=1.N1C=CC=CC=1.[C:38](OC(=O)C)(=[O:40])[CH3:39].CC(O)=O>C1COCC1.CCOC(C)=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH3:12])[CH:7]=[C:6]2[C:13]1[N:23]([CH2:24][O:25][CH2:26][CH2:27][Si:28]([CH3:30])([CH3:29])[CH3:31])[C:16]2=[N:17][CH:18]=[C:19]([CH2:21][NH:22][C:38](=[O:40])[CH3:39])[N:20]=[C:15]2[CH:14]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 1049PyridineHCID 7918Acetic AnhydrideHCID 58009787HCID 58009787, compound

Product 1

HCID 58010206HCID 58010206, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 8028
Tetrahydrofuran
Solvent
HCID 8857Ethyl AcetateSolvent

Procedure

(6-(5-Methoxy-1-methyl-1H-indol-3-yl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl)methanamine (0.185 g, 0.423 mmol) in THF (5 mL) was treated with pyridine (0.044 mL, 0.55 mmol) and acetic anhydride (0.044 mL, 0.47 mmol). The mixture was stirred for about 5 min at ambient temperature and treated with AcOH (0.024 mL, 0.42 mmol). The mixture was diluted with EtOAc (20 mL) and washed with water (15 mL) and brine (10 mL). The organic solution was dried over anhydrous MgSO4, filtered, and concentrated to give N-((6-(5-methoxy-1-methyl-1H-indol-3-yl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl)methyl)acetamide (0.202 g, 100%): LC/MS (Table 2, Method a) Rt=2.63 min; MS m/z: 480 (M+H)+.

Workup

  1. washwashed with water (15 mL) and brine (10 mL)
  2. dry with materialThe organic solution was dried over anhydrous MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-daaa193d629a4c2794cd4f452b01c0a6
Source dataset
uspto-grants-2016_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09365579B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes