tert-Butyl methyl ether → N2-[amino(imino)methyl]-N2-methyl-N-[3-(triphenylphosphonio)-propyl]glycinamide chloride

HRID 58336

Reaction equation

HRID 58336 reaction equation
CNCC(NCC[CH2:9][P+:10]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=O.[Cl-:29].Cl.[N:31]1([C:36](=[NH:38])[NH2:37])[CH:35]=CC=N1.C([N:42]([CH2:46][CH3:47])[CH:43]([CH3:45])C)(C)C.C([O:52]C)(C)(C)C>CN(C)C=O.C(Cl)Cl>[NH2:37][C:36](=[NH:38])[N:31]([CH3:35])[CH2:45][C:43]([NH:42][CH2:46][CH2:47][CH2:9][P+:10]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)([C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:52].[Cl-:29]

Participants

7

Reactant 4

HCID 15413tert-Butyl methyl etherHCID 81531Diisopropylethylamine3×HCID 2734672Pyrazole-1-carboxamidine monohydrochloride3×HCID 131737006N2-methyl-N-[3-(triphenylphosphonio)propyl]glycinamide chloride

Product 1

HCID 71534814N2-[amino(imino)methyl]-N2-methyl-N-[3-(triphenylphosphonio)-propyl]glycinamide chlorideYield 100%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of N2-methyl-N-[3-(triphenylphosphonio)propyl]glycinamide chloride (7.65 g, 17.9 mmol) in N,N-dimethylformamide (15 mL) was added 1-H-pyrazole-1-carboximidamide hydrochloride (2.76 g, 18.8 mmol) and N,N-diisopropylethylamine (3.28 mL, 18.8 mmol). The mixture was stirred overnight at room temperature. After stirring overnight, the reaction was not complete, and additional 1-H-pyrazole-1-carboximidamide hydrochloride (394 mg, 2.69 mmol) and N,N-diisopropylethylamine (0.47 mL, 2.69 mmol) were added. After 8 hours, additional 1-H-pyrazole-1-carboximidamide hydrochloride (338 mg, 2.3 mmol) and N,N-Diisopropylethylamine (0.40 mL, 2.3 mmol) were added again. The mixture was stirred overnight again. The reaction was diluted with methylene chloride (30 mL), and then the solution was added to a flask containing a rapidly stirring mixture of methylene chloride (15 mL) and methyl t-butyl ether (61 mL) to precipitate the product. The supernatant was decanted, and the product was dried under high vacuum at 35° C. to give the title compound (9.4 g, 100% yield about 80% pure) as a crude light yellow solid.

Workup

  1. stirringAfter stirring overnight
  2. waitAfter 8 hours
  3. stirringThe mixture was stirred overnight again
  4. additionthe solution was added to a flask
  5. additioncontaining
  6. stirringa rapidly stirring
  7. customto precipitate the product
  8. customThe supernatant was decanted
  9. customthe product was dried under high vacuum at 35° C.

Sources & evidence

ORD record
ord-b3e209c1fdb444269169df055d48110e
Source dataset
uspto-grants-2016_09
Patent number
US09434753B2

Linked notes

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