Diisopropylethylamine → HCID 59376879, compound

HRID 1771868Notes

Reaction equation

HRID 1771868 reaction equation
[CH:1]([C:4]1[CH:5]=[CH:6][C:7]2[C:12]([NH:13][C:14]3[CH:15]=[C:16]([CH:20]=[CH:21][CH:22]=3)[C:17](O)=[O:18])=[N:11][CH:10]=[N:9][C:8]=2[N:23]=1)([CH3:3])[CH3:2].[NH2:24][C:25]1[CH:30]=[CH:29][C:28]([S:31][C:32]2[CH:37]=[CH:36][C:35]([NH:38][C:39](=[O:45])[O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[CH:34][CH:33]=2)=[C:27]([NH:46][C:47]2[C:48]3[CH:56]=[CH:55][C:54]([CH:57]([CH3:59])[CH3:58])=[N:53][C:49]=3[N:50]=[CH:51][N:52]=2)[CH:26]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CS(C)=O.O>[CH:57]([C:54]1[CH:55]=[CH:56][C:48]2[C:47]([NH:46][C:27]3[CH:26]=[C:25]([NH:24][C:17](=[O:18])[C:16]4[CH:20]=[CH:21][CH:22]=[C:14]([NH:13][C:12]5[C:7]6[CH:6]=[CH:5][C:4]([CH:1]([CH3:2])[CH3:3])=[N:23][C:8]=6[N:9]=[CH:10][N:11]=5)[CH:15]=4)[CH:30]=[CH:29][C:28]=3[S:31][C:32]3[CH:37]=[CH:36][C:35]([NH:38][C:39](=[O:45])[O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[CH:34][CH:33]=3)=[N:52][CH:51]=[N:50][C:49]=2[N:53]=1)([CH3:59])[CH3:58]

Participants

7

Reactant 4

HCID 81531Diisopropylethylamine2×HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)4×HCID 59376826HCID 59376826, compoundHCID 59376905HCID 59376905, compound

Product 1

HCID 59376879HCID 59376879, compoundYield 63%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

To a solution of the product from Example 7B (25.8 mg, 0.084 mmol) in DMSO (2.0 mL) were added the product from Example 2A (40 mg, 0.084 mmol), HATU (31.8 mg, 0.084 mmol), and Hunigs base (56 μL, 0.318 mmol), and the mixture was stirred at room temperature for 24 hours. Additional HATU (39.5 mg, 0.104 mmol), and Hunigs base (50 μL, 0.282 mmol) were added and the reaction was stirred for 48 hours. Added more HATU (39.5 mg, 0.104 mmol) and heated at 45° C. for 8 hours. Added more HATU (39.5 mg, 0.104 mmol) and stirred overnight at room temperature. Water was added and the product was collected by filtration. Purification by chromatography on silica gel eluting with (0% to 5% methanol in dichloromethane) gave the title compound (40 mg, 63% yield).

Workup

  1. stirringthe reaction was stirred for 48 hours
  2. temperatureheated at 45° C. for 8 hours
  3. stirringstirred overnight at room temperature
  4. filtrationthe product was collected by filtration
  5. customPurification by chromatography on silica gel eluting with (0% to 5% methanol in dichloromethane)

Sources & evidence

ORD record
ord-22677a8433b847eba5aebc0eda475199
Source dataset
uspto-grants-2016_02
Patent number
US09249138B2

Reaction notes

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