1-(Oxetan-2-yl)methanamine → HCID 59840938, compound

HRID 424763Notes

Reaction equation

HRID 424763 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH3:29])[C:5]2[N:10]=[C:9]([C:11]3[N:15]([C:16]4[C:21]([Cl:22])=[CH:20][CH:19]=[CH:18][N:17]=4)[N:14]=[C:13]([C:23]([F:26])([F:25])[F:24])[CH:12]=3)[O:8][C:7](=[O:27])[C:6]=2[CH:28]=1.[NH2:30][CH2:31][CH:32]1[CH2:35][CH2:34][O:33]1>O1CCCC1>[Cl:1][C:2]1[CH:28]=[C:6]([C:7]([NH:30][CH2:31][CH:32]2[CH2:35][CH2:34][O:33]2)=[O:27])[C:5]([NH:10][C:9]([C:11]2[N:15]([C:16]3[C:21]([Cl:22])=[CH:20][CH:19]=[CH:18][N:17]=3)[N:14]=[C:13]([C:23]([F:25])([F:24])[F:26])[CH:12]=2)=[O:8])=[C:4]([CH3:29])[CH:3]=1

Participants

4

Reactant 2

HCID 202939311-(Oxetan-2-yl)methanamine2×HCID 231503516-chloro-2-[2-(3-chloro-pyridin-2-yl)-5-trifluoromethyl-2H-pyrazol-3-yl]-8-methylbenzo[d][1,3]oxazin-4-one

Product 1

HCID 59840938HCID 59840938, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 6-chloro-2-[1-(3-chloro-2-pyridinyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl]-8-methyl-4H-3,1-benzoxazin-4-one (200 mg, 0.45 mmol) (prepared according to WO 02/48115, example 2D) in tetrahydrofurane (4 ml), is added 2-aminomethyloxetane (the product of step 2) (79 mg, 0.91 mmol), and the mixture is heated to reflux for 30 minutes. The solution is allowed to cool to ambient temperature and the solvent evaporated in vacuo. The residue is purified by prep. HPLC (hexane/ethyl acetate gradient on LiChrospher Si 60, Merck NW25 column) to afford 180 mg (71%) of the title compound as a white solid. [1H-NMR (CDCl3): 10.21 (s, 1H), 8.48 (d, 1H), 7.88 (d, 1H), 7.41 (m, 1H), 7.32 (s, 1H), 7.29 (m, 2H), 6.63 (m, 1H), 4.98 (m, 1H), 4.68 (m, 1H), 4.48 (m, 1H), 3.71 (m, 1H), 3.59 (m, 1H), 2.68 (m, 1H), 2.43 (m, 1H), 2.19 (s, 3H); MS (electrospray ES+): 528, 530 ((M+H)+)].

Workup

  1. temperaturethe mixture is heated
  2. temperatureto reflux for 30 minutes
  3. customthe solvent evaporated in vacuo
  4. customThe residue is purified by prep

Sources & evidence

ORD record
ord-43d6455cdb2640f189c6412b05afd4c4
Source dataset
uspto-grants-2012_01
Patent number
US08106075B2

Reaction notes

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