1-Hydroxybenzotriazole → 2-Chloro-6-(cyclopropylacetyl)-5,6,7,8-tetrahydro-1,6-naphthyridine
Reaction equation
[CH:1]1([CH2:4][C:5]([OH:7])=O)[CH2:3][CH2:2]1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C1C=CC2N(O)N=NC=2C=1.Cl.[Cl:43][C:44]1[CH:53]=[CH:52][C:51]2[CH2:50][NH:49][CH2:48][CH2:47][C:46]=2[N:45]=1.CCN(C(C)C)C(C)C>CN(C=O)C>[Cl:43][C:44]1[CH:53]=[CH:52][C:51]2[CH2:50][N:49]([C:5](=[O:7])[CH2:4][CH:1]3[CH2:2][CH2:3]3)[CH2:48][CH2:47][C:46]=2[N:45]=1Participants
7
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Procedure
To a stirred solution of cyclopropylacetic acid (24 mg, 0.24 mmol) in DMF (1 ml) at room temperature was added HBTU (185 mg, 0.49 mmol) and HOBt (72 mg, 0.53 mmol) sequentially and the resulting solution stirred for 15 mins. 2-Chloro-5,6,7,8-tetrahydro-1,6-naphthyridine hydrochloride (50 mg, 0.24 mmol) and DIPEA (89 μl, 0.53 mmol) in DMF (1 ml) were then added and the resulting mixture stirred at room temperature for 16 hours. The reaction mixture was evaporated to dryness and the residue was purified by FCC on silica gel (99:1:1 DCM/MeOH/NH3) to provide the title compound (56 mg, 95%).
Workup
- stirringthe resulting mixture stirred at room temperature for 16 hours
- customThe reaction mixture was evaporated to dryness
- customthe residue was purified by FCC on silica gel (99:1:1 DCM/MeOH/NH3)
Sources & evidence
- ORD record
- ord-9705bd990e90403ea3ccc976deb7db88
- Source dataset
- uspto-grants-2014_04
- Patent number
- US08691804B2
Reaction notes
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