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N-methyl-2-pyrrolidone → N-((4S,6S)-4-(5-((6-chlorobenzo[d]oxazol-2-yl)amino)-2-fluorophenyl)-4-methyl-6-(trifluoromethyl)-5,6-dihydro-4H-1,3-oxazin-2-yl)benzamide

HRID 930291
Notes
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Reaction equation

HRID 930291 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([F:29])=[C:6]([C@:8]2([CH2:27]F)[CH2:13][C@@H:12]([C:14]([F:17])([F:16])[F:15])[O:11][C:10]([NH:18][C:19](=[O:26])[C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[N:9]2)[CH:7]=1.Cl[C:31]1[O:32][C:33]2[CH:39]=[C:38]([Cl:40])[CH:37]=[CH:36][C:34]=2[N:35]=1.NC1C=CC(F)=C([C@]2(C)C[C@@H](C(F)(F)F)OC(NC(=O)C3C=CC=CC=3)=N2)C=1.CN1C(=O)CCC1>O.CCOC(C)=O>[Cl:40][C:38]1[CH:37]=[CH:36][C:34]2[N:35]=[C:31]([NH:1][C:2]3[CH:3]=[CH:4][C:5]([F:29])=[C:6]([C@:8]4([CH3:27])[CH2:13][C@@H:12]([C:14]([F:16])([F:15])[F:17])[O:11][C:10]([NH:18][C:19](=[O:26])[C:20]5[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=5)=[N:9]4)[CH:7]=3)[O:32][C:33]=2[CH:39]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 13387N-methyl-2-pyrrolidoneHCID 771752,6-DichlorobenzoxazoleHCID 86732108N-((4S,6S)-4-(5-amino-2-fluorophenyl)-4-(fluoromethyl)-6-(trifluoromethyl)-5,6-dihydro-4H-1,3-oxazin-2-yl)benzamideHCID 86732123N-((4S,6S)-4-(5-amino-2-fluorophenyl)-4-methyl-6-(trifluoromethyl)-5,6-dihydro-4H-1,3-oxazin-2-yl)benzamide

Product 1

HCID 86732122
N-((4S,6S)-4-(5-((6-chlorobenzo[d]oxazol-2-yl)amino)-2-fluorophenyl)-4-methyl-6-(trifluoromethyl)-5,6-dihydro-4H-1,3-oxazin-2-yl)benzamide
Yield 72.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of N-((4S,6S)-4-(5-amino-2-fluorophenyl)-4-methyl-6-(trifluoromethyl)-5,6-dihydro-4H-1,3-oxazin-2-yl)benzamide (0.200 g, 0.506 mmol, prepared as described in Example 1 Step 9 but using N-((4S,6S)-4-(5-bromo-2-fluorophenyl)-4-methyl-6-(trifluoromethyl)-5,6-dihydro-4H-1,3-oxazin-2-yl)benzamide 4g), 2,6-dichlorobenzoxazole (0.133 g, 0.708 mmol), potassium carbonate (4l, 0.126 g, 0.911 mmol) and NMP (2 mL) was stirred at 120° C. for 4.5 h, the mixture was diluted with water and EtOAc. The organic layer was washed with water and brine, dried over Na2SO4 and concentrated in vacuo. The crude was purified by silica gel chromatography: 40 g, 0-30% DCM-hexane in 15 min. The product was obtained as a white solid (0.200 g). MS m/z=547 [M+H]+. Calculated for C26H19ClF4N4O3: 546.9.

Workup

  1. washThe organic layer was washed with water and brine
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. customThe crude was purified by silica gel chromatography
  5. wait40 g, 0-30% DCM-hexane in 15 min

Sources & evidence

ORD record
ord-5fa83e07457a48e58406894270011b2c
Source dataset
uspto-grants-2016_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09296734B2

Reaction notes

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