Methanol → HCID 87267754, compound
Reaction equation
CC(OC(N[C:9]1[S:13][C:12]2[CH:14]=[C:15]([C:18]([OH:20])=[O:19])[CH:16]=[CH:17][C:11]=2[N:10]=1)=O)(C)C.[F:21][C:22]1[C:27]([F:28])=[C:26]([F:29])[C:25]([F:30])=[C:24]([F:31])[C:23]=1O.C1(N=C=N[CH:42]2[CH2:47][CH2:46]CCC2)CCCCC1.[CH3:48]O.CC[O:52][C:53](C)=[O:54]>>[C:47]([O:54][C:53]([C:9]1[S:13][C:12]2[CH:14]=[C:15]([C:18]([O:20][C:23]3[C:22]([F:21])=[C:27]([F:28])[C:26]([F:29])=[C:25]([F:30])[C:24]=3[F:31])=[O:19])[CH:16]=[CH:17][C:11]=2[N:10]=1)=[O:52])([CH3:46])([CH3:42])[CH3:48]Participants
Conditions
- Temperature
- 45 °C
Procedure
To a suspended solution of 2-N—BOC-amino-4-benzothiazole-6-carboxylic acid (2.05 g, 6.97 mmol) and 2,3,4,5,6-pentafluorophenol (1.92 g, 10.4 mmol) in EtOAc (60 mL) was added 1,3-dicyclohexylcarbodiimide (2.16 g, 10.4 mmol). The mixture was heated to 45° C. for 16 hours. Small amount of MeOH was added to the mixture and the solid was removed by filtration. The filtrate was concentrated in vacuo to give pentafluorophenyl 2-(tert-butoxycarbonyl)benzo[d]thiazole-6-carboxylate as a pink material (3.50 g), which was used in the next step without further purification. A solution of pentafluorophenyl 2-(tert-butoxycarbonyl)benzo[d]thiazole-6-carboxylate (1.0 g, 2.2 mmol) and anhydrous hydrazine (0.35 ml, 11 mmol) in THF (30 mL) was stirred at room temperature for 6 hours. The mixture was then concentrated in vacuo and the residue was washed with CHCl3 containing small amount of MeOH. The solid was collected by filtration to give the product as a light yellow solid (0.30 g, 45% yield). MS (ESI pos. ion) m/z: calc'd for: C13H16N4O3S: 308.0. found: 309.0.
Workup
- customthe solid was removed by filtration
- concentrationThe filtrate was concentrated in vacuo
Sources & evidence
- ORD record
- ord-8462af7fd19e49adb74e42e8636dcd00
- Source dataset
- uspto-grants-2011_04
- Patent number
- US07928140B2
Reaction notes
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