Methyl iodide → HCID 66614348, compound

HRID 510087Notes

Reaction equation

HRID 510087 reaction equation
[NH2:1][C:2]1[N:10]=[C:9]([C:11]2[C:19]3[C:14](=[N:15][CH:16]=[CH:17][CH:18]=3)[N:13]([CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[F:27])[N:12]=2)[N:8]=[C:7]2[C:3]=1[NH:4][C:5](=[O:33])[N:6]2[CH2:28][C:29]([F:32])([F:31])[F:30].[CH3:34]CN(P1(N(C)CCCN1C)=NC(C)(C)C)CC.IC>CN(C)C=O>[NH2:1][C:2]1[N:10]=[C:9]([C:11]2[C:19]3[C:14](=[N:15][CH:16]=[CH:17][CH:18]=3)[N:13]([CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[F:27])[N:12]=2)[N:8]=[C:7]2[C:3]=1[N:4]([CH3:34])[C:5](=[O:33])[N:6]2[CH2:28][C:29]([F:32])([F:31])[F:30]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 35138512-((1,1-Dimethylethyl)imino)-N,N-diethylhexahydro-1,3-dimethyl-2lambda5-1,3,2-diazaphosphorin-2-amineHCID 66614606HCID 66614606, compound

Product 1

HCID 66614348HCID 66614348, compoundYield 36.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
0 °C

Procedure

80 mg (0.175 mmol) of the compound from example 36 and 48 mg (0.175 mmol) of BEMP were initially charged in 10 ml of dimethylformamide, and a solution of 25 mg (0.175 mmol) of iodomethane in 2 ml of dimethylformamide was added dropwise at 0° C. within 10 min. The mixture was stirred at 0° C. for 20 min. Subsequently, the reaction solution was concentrated under reduced pressure and the residue was purified by means of preparative HPLC (eluent: methanol/water, gradient 30:70→90:10). 30 mg of the title compound were obtained (35% of theory).

Workup

  1. concentrationSubsequently, the reaction solution was concentrated under reduced pressure
  2. customthe residue was purified by means of preparative HPLC (eluent: methanol/water, gradient 30:70→90:10)

Sources & evidence

ORD record
ord-e9fd92fd3a744b1abafeffd826e690b1
Source dataset
uspto-grants-2015_08
Patent number
US09096592B2

Reaction notes

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