1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 178504762, compound

HRID 2304908Notes

Reaction equation

CN(C)CCCN=C=NCC.[NH:12]1[C:16]2[CH2:17][CH2:18][CH:19]([C:21]([OH:23])=O)[CH2:20][C:15]=2[N:14]=[CH:13]1.ON1C2C=CC=CC=2N=N1.[CH3:34][S:35]([C:38]1[CH:45]=[CH:44][C:41]([CH2:42][NH2:43])=[CH:40][CH:39]=1)(=[O:37])=[O:36].C(N(C(C)C)C(C)C)C>CN(C=O)C>[CH3:34][S:35]([C:38]1[CH:45]=[CH:44][C:41]([CH2:42][NH:43][C:21]([CH:19]2[CH2:18][CH2:17][C:16]3[NH:12][CH:13]=[N:14][C:15]=3[CH2:20]2)=[O:23])=[CH:40][CH:39]=1)(=[O:36])=[O:37]

Participants

Conditions

Temperature: 0 °C

Procedure

At 0° C. 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide (0.23 g, 1.184 mmol) was added to a solution of 4,5,6,7-tetrahydro-1H-benzimidazole-5-carboxylic acid (024 g, 1.184 mmol) and 1-hydroxybenzotriazole (0.16 g, 1.184 mmol) in DMF (5 ml). The reaction mixture was stirred for 20 min at 0° C. 4-(Methylsulfonyl)benzylamine (0.26 g, 1.184 mmol) and ethyldiisopropylamine (0.90 ml, 5.211 mmol) were added successively. The reaction mixture was stirred for 16 hours, while it was warming up to room temperature. The solvent was removed in vacuo. The crude product was purified filtered through SepPack® (5 g), using 1% TFA in water/acetonitrile (80:40) as eluent. The resulting mixture was purified by flash chromatography on silica (40 g), using DCM/methanol/25% aqueous ammonia (50:10:1) as eluent, to give 0.32 g of the title compound.

Workup

customAt 0° C
stirringThe reaction mixture was stirred for 16 hours, while it
temperaturewas warming up to room temperature
customThe solvent was removed in vacuo
customThe crude product was purified
filtrationfiltered through SepPack® (5 g)
customThe resulting mixture was purified by flash chromatography on silica (40 g)

Sources & evidence

ORD record: ord-f6360e22de6e419bbe973589376f59d6
Source dataset: uspto-grants-2002_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06437147B1

Reaction notes

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