Hydrazine hydrate (1:1) → HCID 90024362, compound

HRID 1048701Notes

Reaction equation

HRID 1048701 reaction equation
[F:1][C:2]([F:33])([F:32])[C:3]1[CH:4]=[C:5]([C:9]#[C:10][C:11]2[N:15]3[CH:16]=[CH:17][CH:18]=[CH:19][C:14]3=[N:13][C:12]=2[CH2:20][N:21]2C(=O)C3C(=CC=CC=3)C2=O)[CH:6]=[CH:7][CH:8]=1.O.NN>C(O)C>[F:33][C:2]([F:1])([F:32])[C:3]1[CH:4]=[C:5]([C:9]#[C:10][C:11]2[N:15]3[CH:16]=[CH:17][CH:18]=[CH:19][C:14]3=[N:13][C:12]=2[CH2:20][NH2:21])[CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 118195079HCID 118195079, compound

Product 1

HCID 90024362HCID 90024362, compoundYield 73.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1.41 g (3.08 mmol) of 2-((3-((3-(trifluoromethyl)phenyl)ethynyl) imidazo[1,2-a]pyridin-2-yl)methyl) isoindoline-1,3-dione were solubilised in 30 ml of ethanol with magnetic stirring, 0.978 ml (30.8 mmol) of hydrazine monohydrate were added. The mixture gradually became milky and was stirred at r.t. for 1.5 h. The suspended solid was isolated by filtration and washed with 2×25 ml of ethanol. The filtrate was concentrated in vacuo. The residue was triturated in 20 ml of ethanol, the solid was isolated by filtration and the filtrate concentrated in vacuo in order to obtain 0.715 g (yield=69%) of (3-((3-(trifluoromethyl)phenyl)ethynyl)imidazo[1,2-a]pyridin-2-yl)methanamine as a pale yellow solid. LC-MS: m/z=316 (MH+); UV purity at 254 nm=94%. 1H NMR (300 MHz, DMSO) δ 8.73 (d, J=6.7 Hz, 1H), 8.12 (s, 1H), 7.98 (d, J=7.7 Hz, 1H), 7.82-7.63 (m, 3H), 7.49-7.40 (m, 1H), 7.13 (td, J=6.8, 1.1 Hz, 1H), 3.96 (s, 2H).

Workup

  1. additionwere added
  2. customThe suspended solid was isolated by filtration
  3. washwashed with 2×25 ml of ethanol
  4. concentrationThe filtrate was concentrated in vacuo
  5. customThe residue was triturated in 20 ml of ethanol
  6. customthe solid was isolated by filtration
  7. concentrationthe filtrate concentrated in vacuo in order

Sources & evidence

ORD record
ord-c91e0d29a4424fdeb806f686e54a79c2
Source dataset
uspto-grants-2016_07
Patent number
US09381191B2

Reaction notes

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