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Ethanolamine → N-(2-hydroxyethyl)-1-[(6-methoxy-5-methyl-pyrimidin-4-yl)methyl]pyrrolo[3,2-b]pyridine-3-carboxamide

HRID 1753233
Notes
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Reaction equation

HRID 1753233 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[CH:7][N:6]=[C:5]([CH2:9][N:10]2[C:18]3[C:13](=[N:14][CH:15]=[CH:16][CH:17]=3)[C:12]([C:19]([OH:21])=O)=[CH:11]2)[C:4]=1[CH3:22].C(N(CC)CC)C.CCCP1(OP(CCC)(=O)OP(CCC)(=O)O1)=O.[CH2:48]([CH2:50][NH2:51])[OH:49]>C(Cl)Cl>[OH:49][CH2:48][CH2:50][NH:51][C:19]([C:12]1[C:13]2=[N:14][CH:15]=[CH:16][CH:17]=[C:18]2[N:10]([CH2:9][C:5]2[C:4]([CH3:22])=[C:3]([O:2][CH3:1])[N:8]=[CH:7][N:6]=2)[CH:11]=1)=[O:21]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 700EthanolamineHCID 8471TriethylamineHCID 111923Propylphosphonic anhydrideHCID 1178190601-((6-methoxy-5-methylpyrimidin-4-yl)methyl)-1H-pyrrolo[3,2-b]pyridine-3-carboxylic acid

Product 1

HCID 72792765N-(2-hydroxyethyl)-1-[(6-methoxy-5-methyl-pyrimidin-4-yl)methyl]pyrrolo[3,2-b]pyridine-3-carboxamideYield 45%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

See FIG. 18(a). 1-((6-methoxy-5-methylpyrimidin-4-yl)methyl)-1H-pyrrolo[3,2-b]pyridine-3-carboxylic acid (1 g, 3.35 mmol) was taken in DCM (20 mL) to get a suspension. Triethyl amine (1.394 mL, 10.06 mmol) was added followed by the addition of 1-Propanephosphonic acid cyclic anhydride (3.991 mL, 6.70 mmol). The reaction mass was stirred at RT for 5 minutes. Ethanol amine (6.02 mL, 10.06 mmol) was added and stirred at RT for 2 h. After completion of the reaction, diluted with DCM and then washed with water and brine solution. The organic layer was separated, dried, evaporated and the crude compound was purified by silica gel chromatography. Yield-45%. ES+MS m/z: 342 (M+1). 1H NMR (300 MHz, DMSO-d6) δ ppm 2.24 (s. 3 H ) 3.37-3.64 (m, 4 H ) 3.94 (s, 3 H ) 4.80 (t, J=4.99 Hz, 1 H ) 5.67 (s, 2 H ) 7.24 (dd, J=8.29, 4.52 Hz, 1 H ) 7.92 (d, J=8.10 Hz, 1 H ) 8.23 (s, 1 H ) 8.41 (s, 1 H ) 8.47 (d, J=4.52 Hz, 1 H ) 8.85 (t, J=5.37 Hz, 1 H ).

Workup

  1. customto get a suspension
  2. stirringstirred at RT for 2 h
  3. customAfter completion of the reaction
  4. washwashed with water and brine solution
  5. customThe organic layer was separated
  6. customdried
  7. customevaporated
  8. customthe crude compound was purified by silica gel chromatography

Sources & evidence

ORD record
ord-2dc9c79f37544640a915afcc62ef0713
Source dataset
uspto-grants-2015_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09163020B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes