Dimethylamine → HCID 59699867, compound

HRID 1820106Notes

Reaction equation

HRID 1820106 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][C:5]([N:11]2[CH2:16][CH2:15][N:14]([CH2:17][CH2:18][OH:19])[CH2:13][CH2:12]2)=[C:6]([CH:10]=1)[C:7]([OH:9])=O.[CH3:20][NH:21][CH3:22].F[P-](F)(F)(F)(F)F.N1(O[P+](N2CCCC2)(N2CCCC2)N2CCCC2)C2C=CC=CC=2N=N1>ClCCl.C1COCC1>[Br:1][C:2]1[CH:3]=[N:4][C:5]([N:11]2[CH2:16][CH2:15][N:14]([CH2:17][CH2:18][OH:19])[CH2:13][CH2:12]2)=[C:6]([CH:10]=1)[C:7]([N:21]([CH3:22])[CH3:20])=[O:9]

Participants

6

Reactant 3

HCID 674DimethylamineHCID 2724699PyBOPHCID 59699911HCID 59699911, compound

Product 1

HCID 59699867HCID 59699867, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

630 mg (1.90 mmol) of 5-bromo-2-[4-(2-hydroxy-ethyl)-piperazin-1-yl]-nicotinic acid was suspended in 50 ml of dichloromethane. 6 ml of 2 M dimethylamine in THF and 850 mg (1.63 mmol) of benzotriazol-1-yl-oxytripyrrolidinophosphonium hexafluorophosphate were added and the resulting mixture was stirred for 18 h at ambient temperature. The resulting mixture was diluted with dichloromethane and washed with water. The aqueous phase was extracted with dichloromethane and the organic phases were combined, dried over sodium sulfate and evaporated to afford crude 5-bromo-2-[4-(2-hydroxy-ethyl)-piperazin-1-yl]-N,N-dimethyl-nicotinamide as a pale brown oil containing tris(pyrrolidinyl)phosphoramidate as a contaminant. MS: m/z 357 [MH+].

Workup

  1. washwashed with water
  2. extractionThe aqueous phase was extracted with dichloromethane
  3. dry with materialdried over sodium sulfate
  4. customevaporated

Sources & evidence

ORD record
ord-691befe0001841948612b04406f8b1b0
Source dataset
uspto-grants-2009_10
Patent number
US07601839B2

Reaction notes

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