Dimethylformamide → HCID 18399730, compound

HRID 2184823Notes

Reaction equation

HRID 2184823 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.CN(C)[CH:30]=[O:31].[NH4+].[Cl-]>O1CCCC1.CCCCCC>[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:30]=[O:31])[CH:3]=5)[NH:7][CH:6]=4)[CH2:14][CH2:15]3)[C:24]=2[CH:25]=[CH:26]1

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 25517Ammonium ChlorideHCID 18399720HCID 18399720, compound

Product 1

HCID 18399730HCID 18399730, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

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-butylithium (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-26d06952f8f048c1b63a0f92c9cb58a9
Source dataset
uspto-grants-2002_06
Patent number
US06399616B1

Reaction notes

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