Methoxyacetic Acid → HCID 57597213, compound

HRID 1786951Notes

Reaction equation

HRID 1786951 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][CH2:25][C:26]5[CH:31]=[CH:30][CH:29]=[C:28]([F:32])[CH:27]=5)=[C:20]([Cl:33])[CH:19]=4)=[N:13][CH:12]=[N:11][C:10]=3[CH:9]=2)=[CH:4][CH:3]=1.[CH3:34][O:35][CH2:36][C:37](O)=[O:38].Cl.C(N=C=NCCCN(C)C)C.O.ON1C2C=CC=CC=2N=N1>CN(C)C=O.O.C(N(CC)CC)C>[Cl:33][C:20]1[CH:19]=[C:18]([NH:17][C:14]2[C:15]3[NH:16][C:8]([C:5]4[CH:4]=[CH:3][C:2]([NH:1][C:37](=[O:38])[CH2:36][O:35][CH3:34])=[CH:7][CH:6]=4)=[CH:9][C:10]=3[N:11]=[CH:12][N:13]=2)[CH:23]=[CH:22][C:21]=1[O:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[C:28]([F:32])[CH:27]=1

Participants

8

Reactant 4

HCID 12251Methoxyacetic Acid2×HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride2×HCID 27960291-Hydroxybenzotriazole hydrate2×HCID 57597331HCID 57597331, compound

Product 1

HCID 57597213HCID 57597213, compoundYield 54.9%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

A solution of 6-(4-aminophenyl)-N-{3-chloro-4-[(3-fluorobenzyl)oxy]phenyl}-5H-pyrrolo[3,2-d]pyrimidin-4-amine (100 mg), methoxyacetic acid (29.4 mg), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (94 mg), 1-hydroxybenzotriazole monohydrate (75 mg) and triethylamine (0.23 mL) in N,N-dimethylformamide (5 mL) was stirred at room temperature for 20 hrs. Methoxyacetic acid (29.4 mg), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (94 mg) and 1-hydroxybenzotriazole monohydrate (75 mg) were added to the reaction system, and the mixture was further stirred for 24 hrs. Water was added to the reaction system and the mixture was extracted with ethyl acetate. The organic layer washed with saturated brine, dried over magnesium sulfate and concentrated under reduced pressure, and the residue was separated and purified by column chromatography (basic silica gel, eluent, ethyl acetate→methanol:ethyl acetate=14:85) to give the title compound (63.5 mg) as pale-brown powder crystals.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer washed with saturated brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customthe residue was separated
  6. custompurified by column chromatography (basic silica gel, eluent, ethyl acetate→methanol:ethyl acetate=14:85)

Sources & evidence

ORD record
ord-ac05d5a454f148bd9711858934e1c9f2
Source dataset
uspto-grants-2009_03
Patent number
US07507740B2

Reaction notes

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