Diisopropylethylamine → HCID 89590826, compound

HRID 522395Notes

Reaction equation

HRID 522395 reaction equation
[CH2:1]([O:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[N:12]=[C:11]([O:19][C@@H:20]2[CH2:24][C@@H:23]([C:25]([O:27][CH3:28])=[O:26])[NH2+:22][CH2:21]2)[C:10]=1[C:29]#[C:30][CH2:31][CH2:32][CH2:33][C@@H:34]1[CH2:36][C@H:35]1[O:37][C:38]([NH:40][C@H:41]([C:46](Cl)=[O:47])[C:42]([CH3:45])([CH3:44])[CH3:43])=[O:39])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C.CCOCC>[CH2:1]([O:8][C:9]1[C:18]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[N:12]=[C:11]2[O:19][C@H:20]3[CH2:21][N:22]([C:46](=[O:47])[C@H:41]([C:42]([CH3:44])([CH3:45])[CH3:43])[NH:40][C:38](=[O:39])[O:37][C@@H:35]4[CH2:36][C@H:34]4[CH2:33][CH2:32][CH2:31][C:30]#[C:29][C:10]=12)[C@H:23]([C:25]([O:27][CH3:28])=[O:26])[CH2:24]3)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 131735532HCID 131735532, compound

Product 1

HCID 89590826HCID 89590826, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of the product of step 3 in DMF (52 mL) at 0° C. was added DIPEA (3.1 mL) and HATU (1.64 g). The mixture was stirred at room temperature for 2 hours until disappearance of the starting material. The reaction mixture was diluted with Et2O and quenched with water and HCl (1N). The mixture was extracted (3×) with ether. The combined organic phases were washed with water then brine, dried over sodium sulfate, filtered and concentrated. Purification by flash chromatography (ISCO, 0 to 100% ethyl acetate in hexanes) afforded the desired product (1.3 g). LRMS (ES+) m/z 640.45 (M+H)+.

Workup

  1. customquenched with water and HCl (1N)
  2. extractionThe mixture was extracted (3×) with ether
  3. washThe combined organic phases were washed with water
  4. dry with materialbrine, dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification by flash chromatography (ISCO, 0 to 100% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-8cb4e26752214cb481305afec4d56a7e
Source dataset
uspto-grants-2016_05
Patent number
US09328138B2

Reaction notes

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