1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 11948186, compound

HRID 2264852Notes

Reaction equation

HRID 2264852 reaction equation
C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.[CH:22]1([NH2:25])[CH2:24][CH2:23]1.[CH2:26]([O:28][C:29]([C:31]1[CH:32]=[C:33]2[CH:38]=[N:37][N:36]=[C:35]([NH:39][C:40]3[CH:45]=[C:44]([C:46](O)=[O:47])[CH:43]=[CH:42][C:41]=3[O:49][CH3:50])[N:34]2[C:51]=1[CH3:52])=[O:30])[CH3:27]>CN(C=O)C.O>[CH2:26]([O:28][C:29]([C:31]1[CH:32]=[C:33]2[CH:38]=[N:37][N:36]=[C:35]([NH:39][C:40]3[CH:45]=[C:44]([C:46](=[O:47])[NH:25][CH:22]4[CH2:24][CH2:23]4)[CH:43]=[CH:42][C:41]=3[O:49][CH3:50])[N:34]2[C:51]=1[CH3:52])=[O:30])[CH3:27]

Participants

7

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 69828CyclopropylamineHCID 757711-HydroxybenzotriazoleHCID 68441041HCID 68441041, compound

Product 1

HCID 11948186HCID 11948186, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a suspension of HOBt (30 mg, 0.20 mmol), EDCI (30 mg, 0.16 mmol), cyclopropyl amine (20 uL, 0.29 mmol) in DMF (0.5 mL) at RT was added 4-(5-carboxy-2-methoxy-phenylamino)-6-methyl-pyrrolo[1,2-d][1,2,4]triazine-7-carboxylic acid ethyl ester (13 mg, 0.035 mmol). The reaction was stirred overnight. Water (1 mL) was added and the precipitate collected. The product was purified by flash chromatography on silica gel (1-3% MeOH in CH2Cl2) giving the title compound, 7 mg, as a yellowish solid. HPLC (condition A) tR 4.37 min. MS m/z 410 [M+H]+.

Workup

  1. customthe precipitate collected
  2. customThe product was purified by flash chromatography on silica gel (1-3% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-c0288e854a134ae5882eebc37611cfee
Source dataset
uspto-grants-2010_12
Patent number
US07855288B2

Reaction notes

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