2,6-Difluorobenzaldehyde → trans-N-(7-Chloro-14-fluoro-2,3,4,14b-tetrahydro-1H-dibenzo[b,f]pyrido[1,2-d][1,4]oxazepin-1-yl)-2,2,2-trifluoroacetamide

HRID 16182

Reaction equation

HRID 16182 reaction equation
[Cl:1][C:2]1[CH:28]=[CH:27][C:5]2[O:6][C:7]3[C:25](F)=[CH:24][CH:23]=[CH:22][C:8]=3[C@@H:9]3[C@H:14]([NH:15][C:16](=[O:21])[C:17]([F:20])([F:19])[F:18])[CH2:13][CH2:12][CH2:11][N:10]3[C:4]=2[CH:3]=1.[F:29]C1C=CC=C(F)C=1C=O>>[Cl:1][C:2]1[CH:28]=[CH:27][C:5]2[O:6][C:7]3[CH:25]=[CH:24][CH:23]=[C:22]([F:29])[C:8]=3[C@@H:9]3[C@H:14]([NH:15][C:16](=[O:21])[C:17]([F:19])([F:18])[F:20])[CH2:13][CH2:12][CH2:11][N:10]3[C:4]=2[CH:3]=1

Participants

3

Reactant 2

HCID 1362842,6-DifluorobenzaldehydeHCID 86599895HCID 86599895, compound

Product 1

HCID 86599894trans-N-(7-Chloro-14-fluoro-2,3,4,14b-tetrahydro-1H-dibenzo[b,f]pyrido[1,2-d][1,4]oxazepin-1-yl)-2,2,2-trifluoroacetamideYield 6%

Procedure

Preparation according to the procedures described in Example 72 for trans-N-(7-chloro-11-fluoro-2,3,4,14b-tetrahydro-1H-dibenzo[b,f]pyrido[1,2-d][1,4]oxazepin-1-yl)-2,2,2-trifluoroacetamide starting from 2,6-difluorobenzaldehyde (0.54 mL, 5 mmol) delivered the crude title compound. This compound was purified by column chromatography on silica gel with heptanes/ethyl acetate, column chromatography on silica gel with toluene/ethyl acetate=9/1 and finally crystallization from acetonitrile to yield the title compound (136 mg, 6% overall yield). Data: 1H-NMR (400 MHz, DMSO d6) 1.57-1.76 (m, 2H), 1.89-2.04 (m, 2H), 3.09-3.18 (m, 1H), 3.93 (br.d, J=14, 1H), 4.42 (d, J=10, 1H), 4.52-4.62 (m, 1H), 6.74 (dd, J=9, 3, 1H), 6.95-7.16 (m, 4H), 7.27-7.33 (m, 1H), 9.30 (d, J=9, 1H).

Workup

  1. customPreparation
  2. customThis compound was purified by column chromatography on silica gel with heptanes/ethyl acetate, column chromatography on silica gel with toluene/ethyl acetate=9/1 and finally crystallization from acetonitrile

Sources & evidence

ORD record
ord-c1afea6f4fa9422bb53ac1ab8bba45ce
Source dataset
uspto-grants-2010_06
Patent number
US07737136B2

Linked notes

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