1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → HCID 57597295, compound

HRID 1926101Notes

Reaction equation

HRID 1926101 reaction equation
[NH2:1][CH2:2][CH2:3][N:4]1[C:12]2[C:11]([NH:13][C:14]3[CH:19]=[CH:18][C:17]([O:20][C:21]4[CH:26]=[CH:25][CH:24]=[C:23]([O:27][C:28]([F:31])([F:30])[F:29])[CH:22]=4)=[C:16]([CH3:32])[CH:15]=3)=[N:10][CH:9]=[N:8][C:7]=2[CH:6]=[CH:5]1.[CH3:33][S:34]([CH2:37][C:38](O)=[O:39])(=[O:36])=[O:35].Cl.C(N=C=NCCCN(C)C)C.O.ON1C2C=CC=CC=2N=N1>CN(C)C=O.C(OCC)(=O)C.C(N(CC)CC)C>[CH3:33][S:34]([CH2:37][C:38]([NH:1][CH2:2][CH2:3][N:4]1[C:12]2[C:11]([NH:13][C:14]3[CH:19]=[CH:18][C:17]([O:20][C:21]4[CH:26]=[CH:25][CH:24]=[C:23]([O:27][C:28]([F:30])([F:31])[F:29])[CH:22]=4)=[C:16]([CH3:32])[CH:15]=3)=[N:10][CH:9]=[N:8][C:7]=2[CH:6]=[CH:5]1)=[O:39])(=[O:36])=[O:35]

Participants

8

Reactant 4

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 37328412-Methanesulfonylacetic acidHCID 675204315-(2-aminoethyl)-N-{3-methyl-4-[3-(trifluoromethoxy)phenoxy]phenyl}-5H-pyrrolo[3,2-d]pyrimidin-4-amine

Product 1

HCID 57597295HCID 57597295, compoundYield 41.8%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 5-(2-aminoethyl)-N-{3-methyl-4-[3-(trifluoromethoxy)phenoxy]phenyl}-5H-pyrrolo[3,2-d]pyrimidin-4-amine (174 mg), 2-(methylsulfonyl)acetic acid (54 mg), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (112 mg), 1-hydroxybenzotriazole monohydrate (79 mg) and triethylamine (0.273 mL) in N,N-dimethylformamide (7.69 mL) was stirred at room temperature for 16 hrs. The reaction mixture was diluted with ethyl acetate (80 mL), and washed with water (60 mL). The organic layer was dried over magnesium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography (eluent, ethyl acetate:methanol=100:0→92:8), and crystallized from diisopropyl ether to give the title compound (92 mg) as colorless crystals.

Workup

  1. washwashed with water (60 mL)
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customcrystallized from diisopropyl ether

Sources & evidence

ORD record
ord-ea3deb55016a46ed8cf13ab343a99958
Source dataset
uspto-grants-2012_05
Patent number
US08178543B2

Reaction notes

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