1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 3,5-dichloro-4-{[4-(cyclopropylcarbonyl)-1H-pyrrolo[3,2-c]pyridin-1-yl]carbonyl}-N-[2-(dimethylamino)ethyl]benzamide

HRID 2201881Notes

Reaction equation

HRID 2201881 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([Cl:27])[C:10]=1[C:11]([N:13]1[C:21]2[CH:20]=[CH:19][N:18]=[C:17]([C:22]([CH:24]3[CH2:26][CH2:25]3)=[O:23])[C:16]=2[CH:15]=[CH:14]1)=[O:12])[C:5](O)=[O:6].C(N=C=NCCCN(C)C)C.ON1C2C=CC=CC=2N=N1.[CH3:49][N:50]([CH3:54])[CH2:51][CH2:52][NH2:53].C(=O)(O)[O-].[Na+]>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([Cl:27])[C:10]=1[C:11]([N:13]1[C:21]2[CH:20]=[CH:19][N:18]=[C:17]([C:22]([CH:24]3[CH2:25][CH2:26]3)=[O:23])[C:16]=2[CH:15]=[CH:14]1)=[O:12])[C:5]([NH:53][CH2:52][CH2:51][N:50]([CH3:54])[CH3:49])=[O:6]

Participants

7

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 66053N,N-DimethylethylenediamineHCID 757711-HydroxybenzotriazoleHCID 516892Sodium BicarbonateHCID 710615703,5-dichloro-4-{[4-(cyclopropylcarbonyl)-1H-pyrrolo[3,2-c]pyridin-1-yl]carbonyl}benzoic acid

Product 1

HCID 710619193,5-dichloro-4-{[4-(cyclopropylcarbonyl)-1H-pyrrolo[3,2-c]pyridin-1-yl]carbonyl}-N-[2-(dimethylamino)ethyl]benzamideYield 25%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 3,5-dichloro-4-{[4-(cyclopropylcarbonyl)-1H-pyrrolo[3,2-c]pyridin-1-yl]carbonyl}benzoic acid (40 mg, 0.095 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (22 mg, 0.115 mmol) and 15 mg 1-hydroxybenzotriazole (15 mg, 0.115 mmol) in dimethylformamide, was added N,N-dimethylethane-1,2-diamine (8.4 mg, 0.095 mmol). The resulting reaction mixture was stirred at room temperature for about 16 hours. The reaction mixture was poured drop wise into ie-cooled saturated aqueous sodium bicarbonate solution. The precipitated solid was filtered, washed with water and dried under vacuum. The solid thus obtained was triturated with diethyl ether, filtered and dried to get 3,5-dichloro-4-{[4-(cyclopropylcarbonyl)-1H-pyrrolo[3,2-c]pyridin-1-yl]carbonyl}-N-[2-(dimethylamino)ethyl]benzamide (11 mg, 25%).

Workup

  1. customThe resulting reaction mixture
  2. additionThe reaction mixture was poured drop wise
  3. filtrationThe precipitated solid was filtered
  4. washwashed with water
  5. customdried under vacuum
  6. customThe solid thus obtained
  7. customwas triturated with diethyl ether
  8. filtrationfiltered
  9. customdried

Sources & evidence

ORD record
ord-df6b48f56af547e09ba3969cd52d1510
Source dataset
uspto-grants-2016_06
Patent number
US09364466B2

Reaction notes

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