Diisopropylethylamine → HCID 178472404, compound

HRID 2202739Notes

Reaction equation

HRID 2202739 reaction equation
[CH2:1]([O:3][C:4]([C@H:6]1[CH2:11][CH2:10][C@H:9]([N:12]2[C:16]([C:17]([F:20])([F:19])[F:18])=[C:15]([C:21](O)=[O:22])[CH:14]=[N:13]2)[CH2:8][CH2:7]1)=[O:5])[CH3:2].[Cl:24][C:25]1[CH:26]=[N:27][CH:28]=[C:29]([Cl:50])[C:30]=1[CH:31]([O:42][Si:43]([CH2:48][CH3:49])([CH2:46][CH3:47])[CH2:44][CH3:45])[CH2:32][NH:33][CH2:34][C:35]1[CH:40]=[CH:39][C:38]([F:41])=[CH:37][CH:36]=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>CN(C=O)C>[Cl:24][C:25]1[CH:26]=[N:27][CH:28]=[C:29]([Cl:50])[C:30]=1[CH:31]([O:42][Si:43]([CH2:48][CH3:49])([CH2:46][CH3:47])[CH2:44][CH3:45])[CH2:32][N:33]([CH2:34][C:35]1[CH:40]=[CH:39][C:38]([F:41])=[CH:37][CH:36]=1)[C:21]([C:15]1[CH:14]=[N:13][N:12]([C@H:9]2[CH2:10][CH2:11][C@H:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])[CH2:7][CH2:8]2)[C:16]=1[C:17]([F:18])([F:20])[F:19])=[O:22]

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 123438949HCID 123438949, compoundHCID 178472421HCID 178472421, compound

Product 1

HCID 178472404HCID 178472404, compoundYield 108.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of acid D1 (6.22 g, 18.6 mmol) and amine A1 (8.67 g, 20.4 mmol) in DMF (100 mL) were added HATU (8.48 g, 22.3 mmol) and DIPEA (4.74 mL, 27.9 mmol) and the mixture was stirred at room temperature for 5 h. The reaction mixture was quenched with water (200 mL) and extracted with EtOAc (2×100 mL). The combined organic layers were washed with water (100 mL), brine (100 mL), dried over Na2SO4 and concentrated under reduced pressure to afford compound 1-1 (15 g, crude) as a brown gum.

Workup

  1. customThe reaction mixture was quenched with water (200 mL)
  2. extractionextracted with EtOAc (2×100 mL)
  3. washThe combined organic layers were washed with water (100 mL), brine (100 mL)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f3db41d43c134739abe741666573ed87
Source dataset
uspto-grants-2016_06
Patent number
US09365522B2

Reaction notes

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