1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → HCID 57597184, compound

HRID 1926037Notes

Reaction equation

HRID 1926037 reaction equation
Cl.Cl.[NH2:3][CH2:4][C:5]1[NH:13][C:12]2[C:11]([NH:14][C:15]3[CH:20]=[CH:19][C:18]([O:21][CH2:22][C:23]4[CH:28]=[CH:27][CH:26]=[C:25]([F:29])[CH:24]=4)=[C:17]([Cl:30])[CH:16]=3)=[N:10][CH:9]=[N:8][C:7]=2[CH:6]=1.Cl.[CH3:32][N:33]([CH3:40])[CH2:34]/[CH:35]=[CH: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:30][C:17]1[CH:16]=[C:15]([NH:14][C:11]2[C:12]3[NH:13][C:5]([CH2:4][NH:3][C:37](=[O:38])/[CH:36]=[CH:35]/[CH2:34][N:33]([CH3:40])[CH3:32])=[CH:6][C:7]=3[N:8]=[CH:9][N:10]=2)[CH:20]=[CH:19][C:18]=1[O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([F:29])[CH:24]=1

Participants

8

Reactant 4

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 45358758(2E)-4-(Dimethylamino)-2-butenoic acid hydrochlorideHCID 67521251HCID 67521251, compound

Product 1

HCID 57597184HCID 57597184, compoundYield 64.3%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

A solution of 6-(aminomethyl)-N-{3-chloro-4-[(3-fluorobenzyl)oxy]phenyl}-5H-pyrrolo[3,2-d]pyrimidin-4-amine dihydrochloride (150 mg), (2E)-4-(dimethylamino)but-2-enoic acid hydrochloride (105 mg), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (244 mg), 1-hydroxybenzotriazole monohydrate (196 mg) and triethylamine (0.30 mL) in N,N-dimethylformamide (5 mL) was stirred at room temperature for 2 days. Water was added to the reaction system and the mixture was extracted with ethyl acetate. The organic layer was 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, methanol:ethyl acetate=1:9→1:4) to give the title compound (104.2 mg) as pale-brown powder crystals.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was 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, methanol:ethyl acetate=1:9→1:4)

Sources & evidence

ORD record
ord-929ae0784aa84a5592c418c3c130ee6d
Source dataset
uspto-grants-2012_05
Patent number
US08178543B2

Reaction notes

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