Methoxyacetic Acid → HCID 57597361, compound

HRID 1925950Notes

Reaction equation

HRID 1925950 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-564a349a8e0545c597b19d481065ea1e
Source dataset
uspto-grants-2012_05
Patent number
US08178543B2

Reaction notes

Loading…