Dimethylformamide → HCID 18399730, compound

HRID 1019007Notes

Reaction equation

HRID 1019007 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[CH2:11][CH2:12][N:13]1[CH2:18][CH2:17][N:16]([C:19]2[C:24]3[CH:25]=[CH:26][NH:27][C:23]=3[CH:22]=[CH:21][N:20]=2)[CH2:15][CH2:14]1.C([Li])(C)(C)C.CN(C)[CH:35]=[O:36].[NH4+].[Cl-]>O1CCCC1>[NH:27]1[C:23]2[CH:22]=[CH:21][N:20]=[C:19]([N:16]3[CH2:17][CH2:18][N:13]([CH2:12][CH2:11][C:5]4[C:4]5[C:8](=[CH:9][CH:10]=[C:2]([CH:35]=[O:36])[CH:3]=5)[NH:7][CH:6]=4)[CH2:14][CH2:15]3)[C:24]=2[CH:25]=[CH:26]1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 25517Ammonium ChlorideHCID 18399720HCID 18399720, compoundHCID 178418306HCID 178418306, compound

Product 1

HCID 18399730HCID 18399730, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution at −78° C. of 1.5 mmol of the compound obtained in Step 3 in tetrahydrofuran is treated with 9 mmol of tert-butyllithium (1.8M in hexane). After stirring the mixture for 1 hour, 12 mmol of dimethylformamide are added and the mixture is brought to ambient temperature. After reaction for 4 hours, the solution is hydrolysed by a saturated solution of NH4Cl and then extracted with dichloromethane. After treating the organic phase in conventional manner, chromatography of the residue on silica gel enables the expected product to be isolated.

Workup

  1. customis brought to ambient temperature
  2. customAfter reaction for 4 hours
  3. extractionextracted with dichloromethane
  4. additionAfter treating the organic phase in conventional manner, chromatography of the residue on silica gel
  5. customto be isolated

Sources & evidence

ORD record
ord-62af23477a0b41a3abbc3409ed826ab5
Source dataset
uspto-grants-2002_11
Patent number
US06486171B2

Reaction notes

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