Propylphosphonic anhydride → HCID 86732252, compound
Reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([Cl:21])[C:5]([F:20])=[C:6]([C@:8]2([CH3:19])[CH2:13][C@@H:12]([C:14]([F:17])([F:16])[F:15])[O:11][C:10]([NH2:18])=[N:9]2)[CH:7]=1.[C:22]([C:24]1[CH:25]=[CH:26][C:27]([C:30](O)=[O:31])=[N:28][CH:29]=1)#[N:23].C(P1(=O)OP(=O)(CCC)OP(=O)(CCC)O1)CC>>[NH2:18][C:10]1[O:11][C@H:12]([C:14]([F:17])([F:16])[F:15])[CH2:13][C@:8]([C:6]2[CH:7]=[C:2]([NH:1][C:30](=[O:31])[C:27]3[CH:26]=[CH:25][C:24]([C:22]#[N:23])=[CH:29][N:28]=3)[CH:3]=[C:4]([Cl:21])[C:5]=2[F:20])([CH3:19])[N:9]=1Participants
Procedure
To a cooled (ice bath) solution of (4S,6S)-4-(5-amino-3-chloro-2-fluorophenyl)-4-methyl-6-(trifluoromethyl)-5,6-dihydro-4H-1,3-oxazin-2-amine (0.090 g, 0.276 mmol) and 5-cyano-2-pyridinecarboxylic acid (0.060 g, 0.405 mmol) in n,n-Dimethylformamide (1.5 mL) was added dropwise 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane 2,4,6-trioxide (0.352 mL, 0.553 mmol). After stirred for 1.5 h, reaction went to completion. The reaction mixture was quenched with saturated NaHCO3 and diluted with water. The resulted suspension was stirred for 30 min, and filtered. The filter caked was washed with water and purified by Shimadzu HPLC to afford the title compound (0.086 g, 0.189 mmol, 68.3% yield) as off-white solid. MS m/z=456.0 [M+H]+. Calculated for C19H14ClF4N5O2: 455.79
Workup
- customreaction
- customThe reaction mixture was quenched with saturated NaHCO3
- additiondiluted with water
- stirringThe resulted suspension was stirred for 30 min
- filtrationfiltered
- washThe filter caked was washed with water
- custompurified by Shimadzu HPLC
Sources & evidence
- ORD record
- ord-f4c317dacd5a43589f85ebbc2b8dc559
- Source dataset
- uspto-grants-2016_03
- Patent number
- US09296734B2
Reaction notes
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