Diisopropylethylamine → HCID 44241540, compound

HRID 388393Notes

Reaction equation

HRID 388393 reaction equation
CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH2:25]([O:27][C:28]1[CH:29]=[C:30]([C:34]2[N:39]=[CH:38][C:37]([C:40]([OH:42])=O)=[CH:36][N:35]=2)[CH:31]=[CH:32][CH:33]=1)[CH3:26].CCN(C(C)C)C(C)C.[F:52][C:53]([F:66])([F:65])[C:54]1[NH:55][C:56]2[C:61]([CH:62]=1)=[CH:60][C:59]([CH2:63][NH2:64])=[CH:58][CH:57]=2>CN(C=O)C>[CH2:25]([O:27][C:28]1[CH:29]=[C:30]([C:34]2[N:35]=[CH:36][C:37]([C:40]([NH:64][CH2:63][C:59]3[CH:60]=[C:61]4[C:56](=[CH:57][CH:58]=3)[NH:55][C:54]([C:53]([F:66])([F:52])[F:65])=[CH:62]4)=[O:42])=[CH:38][N:39]=2)[CH:31]=[CH:32][CH:33]=1)[CH3:26]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 551138792-[3-(Ethyloxy)phenyl]-5-pyrimidinecarboxylic acid2×HCID 58126817(2-(Trifluoromethyl)-1h-indol-5-yl)methanamine2×

Product 1

HCID 44241540HCID 44241540, compoundYield 45.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

To a stirred solution of HATU (30.3 mg, 0.080 mmol) in DMF (1 ml) was added 2-[3-(ethyloxy)phenyl]-5-pyrimidinecarboxylic acid (Intermediate 7, 10 mg, 0.041 mmol) in DMF (0.5 ml), followed by DIPEA (0.021 ml, 0.120 mmol) and finally {[2-(trifluoromethyl)-1H-indol-5-yl]methyl}amine (Intermediate 4, 10 mg, 0.040 mmol) in DMF (1 ml). The solution was stirred for 24 hrs then DMF was removed using a rotary evaporator. DCM and sodium bicarbonate solution were then added to the residue. The mixture was poured through a phase separation cartridge, the organic layer evaporated to dryness and purified using MDAP to give the title compound as a yellow solid (8 mg);

Workup

  1. customDMF was removed
  2. customa rotary evaporator
  3. additionDCM and sodium bicarbonate solution were then added to the residue
  4. additionThe mixture was poured through a phase separation cartridge
  5. customthe organic layer evaporated to dryness
  6. custompurified

Sources & evidence

ORD record
ord-57df2fd63a79412fbae697c7abc68793
Source dataset
uspto-grants-2013_02
Patent number
US08377941B2

Reaction notes

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