Ammonia → Diisopropyl Ether

HRID 2243369Notes

Reaction equation

HRID 2243369 reaction equation
CO[C:3]([C:5]1[CH:27]=[CH:26][C:8]2[NH:9][C:10]([C:12]3[C:24]4[C:23]5[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=5)[CH:17]([NH-:25])[C:16]=4[CH:15]=[CH:14][CH:13]=3)=[N:11][C:7]=2[CH:6]=1)=[O:4].N1C2N=C[CH:35]=[C:36]([C:37]([OH:39])=O)[C:31]=2[CH:30]=[CH:29]1.[OH2:40].[NH3:41]>NCCCO.CO.[Cl-].[Na+]>[CH:5]([O:40][CH:30]([CH3:31])[CH3:29])([CH3:6])[CH3:3].[OH:39][CH2:37][CH2:36][CH2:35][NH:41][C:3]([C:5]1[CH:27]=[CH:26][C:8]2[NH:9][C:10]([C:12]3[C:24]4[C:23]5[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=5)[CH:17]([NH-:25])[C:16]=4[CH:15]=[CH:14][CH:13]=3)=[N:11][C:7]=2[CH:6]=1)=[O:4]

Participants

8

Reactant 4

HCID 222AmmoniaHCID 962WaterHCID 224774261H-pyrrolo[2,3-b]pyridine-4-carboxylic acidHCID 178497338HCID 178497338, compound

Product 2

HCID 7914Diisopropyl EtherHCID 178514210HCID 178514210, compound

Reagents, catalysts & solvents 2

HCID 90863-Amino-1-propanolSolventHCID 21958396HCID 21958396, compoundSolvent

Conditions

Temperature
170 °C

Procedure

In a 30 ml round-bottomed flask under argon, dissolve 300 mg of [4-(5-methoxycarbonyl-1H-benzimidazol-2-yl)-9H-fluoren-9(R,S)-yl]amide of 1H-pyrrolo[2,3-b]pyridine-4-carboxylic acid, obtained in Example 205, in 5 ml of 3-aminopropanol, and then heat at 170° C. for 2 h 30. The reaction medium is poured into water containing a few ml of ammonia as a 7N solution in sodium chloride methanol, the mixture is extracted with ethyl acetate, and the organic phase is then washed with a saturated solution of sodium chloride, dried over magnesium sulphate and brought to dryness under reduced pressure. The crude solid obtained is purified by flash chromatography on silica gel (40-63 μm), eluting with a mixture of dichloromethane and methanol (95/5 then 9/1 by volume). After formation of a paste with diisopropyl ether, in this way we obtain 38 mg of {{4-{5-[(3-hydroxypropyl)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. extractionthe mixture is extracted with ethyl acetate
  2. washthe organic phase is then washed with a saturated solution of sodium chloride
  3. dry with materialdried over magnesium sulphate
  4. customThe crude solid obtained
  5. customis purified by flash chromatography on silica gel (40-63 μm)
  6. washeluting with a mixture of dichloromethane and methanol (95/5

Sources & evidence

ORD record
ord-1c5f8e7db25140ba98a70e2f907615cd
Source dataset
uspto-grants-2010_03
Patent number
US07674795B2

Reaction notes

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