Acetonitrile → 2-((1R,6S)-3,8-Diazabicyclo[4.2.0]octan-8-yl)-5-chlorobenzo[d]oxazole

HRID 1193084Notes

Reaction equation

HRID 1193084 reaction equation
F[C:2](F)(F)[C:3]1[CH:8]=[CH:7][N:6]=[C:5]([N:9]2[C@@H:16]3[C@@H:11]([CH2:12][CH2:13]N[CH2:15]3)C2)N=1.[Cl:19][C:20]1N=C(C(F)(F)F)C=CN=1.C([O-])([O-])=[O:31].[K+].[K+].CCN(C(C)C)C(C)C.[C:45](#[N:47])[CH3:46]>CN(C=O)C>[C@@H:46]12[N:6]([C:5]3[O:31][C:11]4[CH:12]=[CH:13][C:20]([Cl:19])=[CH:15][C:16]=4[N:9]=3)[CH2:7][C@@H:8]1[CH2:3][CH2:2][NH:47][CH2:45]2

Participants

7

Reactant 5

HCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 81531DiisopropylethylamineHCID 27739122-Chloro-4-(trifluoromethyl)pyrimidineHCID 67116508HCID 67116508, compound

Product 1

HCID 671167812-((1R,6S)-3,8-Diazabicyclo[4.2.0]octan-8-yl)-5-chlorobenzo[d]oxazole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The title compound was prepared in a manner analogous to Intermediate 27, substituting 2,5-dichlorobenzo[d]oxazole for 2-chloro-4-(trifluoromethyl)pyrimidine. In addition, DMF and K2CO3 at 95° C. was substituted for DIPEA and ACN.

Workup

  1. customat 95° C.

Sources & evidence

ORD record
ord-858f1d809a974914ba1d01bf0d266172
Source dataset
uspto-grants-2014_03
Patent number
US08680275B2

Reaction notes

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