Diisopropylethylamine → HCID 86687118, compound

HRID 2282563Notes

Reaction equation

HRID 2282563 reaction equation
[CH3:1][N:2]1[CH2:6][CH2:5][CH2:4][C@@:3]1([CH2:10][O:11][Si:12]([CH:19]([CH3:21])[CH3:20])([CH:16]([CH3:18])[CH3:17])[CH:13]([CH3:15])[CH3:14])[C:7]([OH:9])=O.[F:22][C:23]1[CH:24]=[CH:25][C:26]([NH:29][NH2:30])=[N:27][CH:28]=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>C(Cl)Cl>[F:22][C:23]1[CH:24]=[CH:25][C:26]([NH:29][NH:30][C:7]([C@:3]2([CH2:10][O:11][Si:12]([CH:13]([CH3:14])[CH3:15])([CH:16]([CH3:17])[CH3:18])[CH:19]([CH3:20])[CH3:21])[CH2:4][CH2:5][CH2:6][N:2]2[CH3:1])=[O:9])=[N:27][CH:28]=1

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 199167865-Fluoro-2-hydrazinylpyridineHCID 86687116HCID 86687116, compound

Product 1

HCID 86687118HCID 86687118, compoundYield 90.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of Intermediate 85g (1.08 g, 3.58 mmol), (5-fluoro-pyridin-2-yl)-hydrazine (500 mg, 3.93 mmol) and DIPEA (1.38 g, 10.7 mmol) in DCM (120 mL) was added HATU (2.04 g, 5.37 mmol) and the mixture stirred at RT for 2 h. The solution was washed with 10% aq. K2CO3 solution, brine, dried (MgSO4), and concentrated in vacuo. The residue was purified by FCC, using 0-6% [2M NH3 in MeOH] in DCM, to give the title compound as a pale yellow oil (1.37 g, 90%). LCMS (Method 4): Rt 2.74 min, m/z 425 [MH+].

Workup

  1. washThe solution was washed with 10% aq. K2CO3 solution, brine
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by FCC

Sources & evidence

ORD record
ord-b7f0b80b1fbb4a3a8426765031f1fef1
Source dataset
uspto-grants-2015_09
Patent number
US09139584B2

Reaction notes

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