Dimethylformamide → Diisopropyl Ether

HRID 2243317Notes

Reaction equation

HRID 2243317 reaction equation
C[CH2:2][N:3]=[C:4]=[N:5][CH2:6][CH2:7][CH2:8][N:9]([CH3:11])C.[CH:12]1[CH:13]=[CH:14][C:15]2N(O)N=N[C:16]=2[CH:17]=1.C[N:23]([CH:25]=[O:26])C>>[CH:17]([O:26][CH:7]([CH3:6])[CH3:8])([CH3:16])[CH3:12].[N:5]1[C:6]2[CH:7]=[CH:8][N:9]=[CH:11][C:2]=2[NH:3][C:4]=1[C:17]1[C:16]2[C:13]3[C:12](=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH:25]([NH-:23])[C:15]=2[CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-Hydroxybenzotriazole

Product 2

HCID 7914Diisopropyl EtherHCID 86621028HCID 86621028, compound

Procedure

Carry out the procedure as in Example 14, starting from 200 mg of 4-(3H-imidazo[4,5-c]pyridin-2-yl)-fluorene-9(R,S)-amine, obtained in Example 6, and 138 mg of 2-methyl-quinoline-5-carboxylic acid, which can be obtained according to J. Med. Chem. 2002, 4647, in the presence of 128.4 mg of EDCI and 90.5 mg of HOBT in 5.5 ml of DMF for 20 hours. After purification by washing successively with a saturated aqueous solution of sodium hydrogen carbonate then with water and diisopropyl ether, we obtain 70 mg of [4-(3H-imidazo[4,5-c]pyridin-2-yl)-9H-fluoren-9-yl]amide of 2-methyl-quinoline-5-carboxylic acid, in the form of a pale yellow powder, with the following characteristics:

Workup

  1. customcan be obtained
  2. customAfter purification
  3. washby washing successively with a saturated aqueous solution of sodium hydrogen carbonate

Sources & evidence

ORD record
ord-9eb1b6382c394e86993a04d6a3267f10
Source dataset
uspto-grants-2010_03
Patent number
US07674795B2

Reaction notes

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