Methoxyacetic Acid → HCID 57597361, compound

HRID 1786861Notes

Reaction equation

HRID 1786861 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:16][C:15]3[C:14]([NH:17][C:18]4[CH:23]=[CH:22][C:21]([O:24][C:25]5[CH:26]=[N:27][C:28]([CH3:31])=[CH:29][CH:30]=5)=[C:20]([CH3:32])[CH:19]=4)=[N:13][CH:12]=[N:11][C:10]=3[CH:9]=2)=[CH:4][CH:3]=1.[CH3:33][O:34][CH2:35][C:36](O)=[O:37].O.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C>CN(C)C=O.ClCCl.C(N(CC)CC)C>[CH3:33][O:34][CH2:35][C:36]([NH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:16][C:15]3[C:14]([NH:17][C:18]4[CH:23]=[CH:22][C:21]([O:24][C:25]5[CH:26]=[N:27][C:28]([CH3:31])=[CH:29][CH:30]=5)=[C:20]([CH3:32])[CH:19]=4)=[N:13][CH:12]=[N:11][C:10]=3[CH:9]=2)=[CH:4][CH:3]=1)=[O:37]

Participants

8

Reactant 4

HCID 12251Methoxyacetic AcidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 57597230HCID 57597230, compound

Product 1

HCID 57597361HCID 57597361, compound

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

To a mixture of 6-(4-aminophenyl)-N-{3-methyl-4-[(6-methylpyridin-3-yl)oxy]phenyl}-5H-pyrrolo[3,2-d]pyrimidin-4-amine (40 mg), methoxyacetic acid (0.0145 mL) and 1-hydroxybenzotriazole monohydrate (38 mg) in N,N-dimethylformamide (1.9 mL) were added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (54 mg) and triethylamine (0.079 mL) at room temperature. After stirring overnight at room temperature, the reaction mixture was diluted with dichloromethane (10 mL). The residue was separated and purified by basic silica gel column chromatography (eluent, ethyl acetate:methanol=100:0→ethyl acetate:methanol=85:15) and crystallized from diisopropyl ether to give the title compound (24 mg).

Workup

  1. customThe residue was separated
  2. custompurified by basic silica gel column chromatography (eluent, ethyl acetate:methanol=100:0→ethyl acetate:methanol=85:15)
  3. customcrystallized from diisopropyl ether

Sources & evidence

ORD record
ord-2b9adc720be54eb48d919d4ef7b1d0db
Source dataset
uspto-grants-2009_03
Patent number
US07507740B2

Reaction notes

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