Iodoethane → HCID 66614391, compound

HRID 510082Notes

Reaction equation

HRID 510082 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:28])[NH:6]2.[CH3:29][CH2:30]N(P1(N(C)CCCN1C)=NC(C)(C)C)CC.C(I)C>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[NH:4][C:5](=[O:28])[N:6]2[CH2:29][CH3:30]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 35138512-((1,1-Dimethylethyl)imino)-N,N-diethylhexahydro-1,3-dimethyl-2lambda5-1,3,2-diazaphosphorin-2-amineHCID 666136276-amino-2-(1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl)- 7,9-dihydro-8H-purin-8-one

Product 1

HCID 66614391HCID 66614391, compoundYield 31.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
0 °C

Procedure

200 mg (0.531 mmol) of the compound from example 33 and 146 mg (0.531 mmol) of BEMP were initially charged in 10 ml of dimethylformamide, and a solution of 82 mg (0.531 mmol) of ethyl iodide 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: acetonitrile/water, gradient 10:90→90:10). 67 mg of the title compound were obtained (31% of theory).

Workup

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

Sources & evidence

ORD record
ord-964b39ea5b764909960bf1aaa8202348
Source dataset
uspto-grants-2015_08
Patent number
US09096592B2

Reaction notes

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