Water → Diisopropyl Ether

HRID 2243352Notes

Reaction equation

HRID 2243352 reaction equation
CN(C)CCN.Cl.CN(C)[CH2:10][CH2:11][CH2:12]N=C=NCC.ON1[C:24]2C=CC=[CH:28][C:23]=2N=N1.O.[C:30]([C:33]1[CH:55]=[CH:54][C:36]2[NH:37][C:38](C3C4C5C(=CC=CC=5)C([NH-])C=4C=CC=3)=[N:39][C:35]=2[CH:34]=1)([OH:32])=[O:31]>N1C2N=CC=C(C(O)=O)C=2C=C1.CN(C)C=O>[CH:23]([O:31][CH:11]([CH3:10])[CH3:12])([CH3:28])[CH3:24].[NH:37]1[C:38]2[N:39]=[CH:35][CH:34]=[C:33]([C:30]([OH:32])=[O:31])[C:55]=2[CH:54]=[CH:36]1

Participants

9

Reactant 5

HCID 962WaterHCID 66053N,N-DimethylethylenediamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 178514211HCID 178514211, compound

Product 2

HCID 7914Diisopropyl EtherHCID 224774261H-pyrrolo[2,3-b]pyridine-4-carboxylic acid

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 224774261H-pyrrolo[2,3-b]pyridine-4-carboxylic acidSolvent

Procedure

In a 10 ml round-bottomed flask, dissolve 200 mg of [4-(5-carboxy-1H-benzimidazol-2-yl)-9H-fluoren-9(R,S)-yl]amide of 1H-pyrrolo[2,3-b]pyridine-4-carboxylic acid, obtained in Example 206, in 2.5 ml of dimethylformamide, then add successively 100 μl of N,N-dimethylethylenediamine, 79 mg of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDCI) and 28 mg of 1-hydroxybenzotriazole (HOBT), and then stir for 20 hours at room temperature. Bring the dimethylformamide to dryness, add water, and drain the precipitate that formed and then wash with water and then with a 10% saturated solution of sodium hydrogen carbonate and, finally, with water. The crude solid obtained is dried and then purified by flash chromatography on silica gel (40-63 μm), eluting with a mixture of dichloromethane and ammonia as a 7N solution in methanol (95/5 then 9/1 by volume). After formation of a paste with diisopropyl ether, in this way we obtain 103 mg of 4-[5-(2-dimethylaminoethyl)aminocarbonyl-1H-benzimidazol-2-yl)-9H-fluoren-9(R,S)-yl]amide of 1H-pyrrolo[2,3-b]pyridine-4-carboxylic acid, in the form of an off-white powder with the following characteristics:

Workup

  1. customthat formed
  2. washwash with water
  3. customThe crude solid obtained
  4. customis dried
  5. custompurified by flash chromatography on silica gel (40-63 μm)
  6. washeluting with a mixture of dichloromethane and ammonia as a 7N solution in methanol (95/5

Sources & evidence

ORD record
ord-a087672eedcd4aa2a3f5b997072474a0
Source dataset
uspto-grants-2010_03
Patent number
US07674795B2

Reaction notes

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