1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 69132695, compound

HRID 349504Notes

Reaction equation

HRID 349504 reaction equation
C[O:2][C:3]([C:5]1[C:13]2[N:12]=[C:11]([C:14]3[CH:19]=[CH:18][C:17]([NH2:20])=[CH:16][C:15]=3[CH2:21][CH2:22][N:23]3[CH2:28][CH2:27][O:26][CH2:25][CH2:24]3)[NH:10][C:9]=2[C:8]([O:29][CH3:30])=[CH:7][CH:6]=1)=O.[Cl:31][C:32]1[N:33]=[CH:34][N:35]([CH2:38][CH2:39][CH2:40][NH2:41])[C:36]=1[Cl:37].CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1>C1COCC1.O.CN(C1C=CN=CC=1)C>[Cl:31][C:32]1[N:33]=[CH:34][N:35]([CH2:38][CH2:39][CH2:40][NH:41][C:3]([C:5]2[C:13]3[N:12]=[C:11]([C:14]4[CH:19]=[CH:18][C:17]([NH2:20])=[CH:16][C:15]=4[CH2:21][CH2:22][N:23]4[CH2:28][CH2:27][O:26][CH2:25][CH2:24]4)[NH:10][C:9]=3[C:8]([O:29][CH3:30])=[CH:7][CH:6]=2)=[O:2])[C:36]=1[Cl:37]

Participants

7

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 68959752HCID 68959752, compoundHCID 69131513HCID 69131513, compound

Product 1

HCID 69132695HCID 69132695, compoundYield 63%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 21881883Oxolane--water (1/1)Solvent

Procedure

2-[(2-morpholinoethyl)-4-amino-phenyl]-7-methoxy-1H-benzoimidazole-4-carboxylic acid methyl ester (22 mg, 0.05 mmol) was dissolved in THF/H2O, LiOHH2O (6.7 mg, 0.16 mmol) was added thereto and stirred at room temperature. The resulting solution was filtered to remove residual LiOHH2O, and the solvent was removed. The residue was dried and dissolved in DMF. Added thereto were 4,5-dichloro-1-(3-aminopropyl)imidazole (12.5 mg, 0.06 mmol), EDCI (30.9 mg, 0.16 mmol), DMAP (65.6 mg, 0.54 mmol) and HOBt (21.8 mg, 0.16 mmol), followed by stirring at room temperature. The resulting solution was extracted with ethyl acetate and concentrated under a reduced pressure. The resulting residue was purified by silica gel chromatography to obtain the title compound (19 mg, 0.03 mmol) in a yield of 63%.

Workup

  1. filtrationThe resulting solution was filtered
  2. customto remove residual LiOHH2O
  3. customthe solvent was removed
  4. customThe residue was dried
  5. dissolutiondissolved in DMF
  6. additionAdded
  7. stirringby stirring at room temperature
  8. extractionThe resulting solution was extracted with ethyl acetate
  9. concentrationconcentrated under a reduced pressure
  10. customThe resulting residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-bb058433fb224ad6b70d1bde5621b2a3
Source dataset
uspto-grants-2007_02
Patent number
US07179832B2

Reaction notes

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