1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → tert-butyl {2-[(3,5-dichloro-4-{[4-(cyclopropylcarbonyl)-1H-pyrrolo[3,2-c]pyridin-1-yl]carbonyl}benzoyl)amino]ethyl}carbamate

HRID 875494Notes

Reaction equation

HRID 875494 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]([OH:7])=O.C(N=C=NCCCN(C)C)C.ON1C2C=CC=CC=2N=N1.[NH2:49][CH2:50][CH2:51][NH:52][C:53](=[O:59])[O:54][C:55]([CH3:58])([CH3:57])[CH3:56].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:49][CH2:50][CH2:51][NH:52][C:53](=[O:59])[O:54][C:55]([CH3:57])([CH3:56])[CH3:58])=[O:7]

Participants

7

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 187201N-BOC-ethylenediamineHCID 516892Sodium BicarbonateHCID 710615703,5-dichloro-4-{[4-(cyclopropylcarbonyl)-1H-pyrrolo[3,2-c]pyridin-1-yl]carbonyl}benzoic acid

Product 1

HCID 86720668tert-butyl {2-[(3,5-dichloro-4-{[4-(cyclopropylcarbonyl)-1H-pyrrolo[3,2-c]pyridin-1-yl]carbonyl}benzoyl)amino]ethyl}carbamateYield 35.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To the stirred mixture of 3,5-dichloro-4-{[4-(cyclopropylcarbonyl)-1H-pyrrolo[3,2-c]pyridin-1-yl]carbonyl}benzoic acid (50 mg, 0.119 mmol), 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide (26.8 mg, 0.14 mmol) and 1-hydroxybenzotriazole (19 mg, 0.14 mmol) in N,N-dimethylformamide, was added tert-butyl (2-aminoethyl)carbamate (19 mg, 0.119 mmol). The reaction mixture was stirred at room temperature for about 16 hours. The reaction mixture was poured drop wise into cold saturated solution of sodium bicarbonate. The precipitated solid was filtered, washed with water and dried. Purification by preparative thin layer chromatography (2% methanol and dichloromethane as eluent) afforded tert-butyl {2-[(3,5-dichloro-4-{[4-(cyclopropylcarbonyl)-1H-pyrrolo[3,2-c]pyridin-1-yl]carbonyl}benzoyl)amino]ethyl}carbamate (23 mg, 35%).

Workup

  1. filtrationThe precipitated solid was filtered
  2. washwashed with water
  3. customdried
  4. customPurification by preparative thin layer chromatography (2% methanol and dichloromethane as eluent)

Sources & evidence

ORD record
ord-7dd45f0d74ff4ee0bda8f6f78595ef3d
Source dataset
uspto-grants-2015_03
Patent number
US08980911B2

Reaction notes

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