Bromomethylcyclopropane → HCID 66614138, compound

HRID 510084Notes

Reaction equation

HRID 510084 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.CCN(P1(N(C)CCCN1C)=N[C:36]([CH3:39])([CH3:38])[CH3:37])CC.BrCC1CC1>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[CH2:37][CH:36]1[CH2:39][CH2:38]1

Participants

5

Reactant 3

HCID 81503BromomethylcyclopropaneHCID 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 66614138HCID 66614138, compoundYield 11.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
0 °C

Procedure

200 mg (0.531 mmol) of the compound from example 33 and 145 mg (0.531 mmol) of BEMP were initially charged in 10 ml of dimethylformamide, and a solution of 71 mg (0.531 mmol) of (bromomethyl)cyclopropane 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). 27 mg of the title compound were obtained (11% 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-1e03f52a1bc743f2bdb376579b30bae6
Source dataset
uspto-grants-2015_08
Patent number
US09096592B2

Reaction notes

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