Cyclopropanecarbonyl chloride → 2-Chloro-6-(cyclopropylcarbonyl)-5,6,7,8-tetrahydro-1,6-naphthyridine

HRID 2361644Notes

Reaction equation

HRID 2361644 reaction equation
Cl.[Cl:2][C:3]1[CH:12]=[CH:11][C:10]2[CH2:9][NH:8][CH2:7][CH2:6][C:5]=2[N:4]=1.CCN(C(C)C)C(C)C.[CH:22]1([C:25](Cl)=[O:26])[CH2:24][CH2:23]1>ClCCl.Cl>[Cl:2][C:3]1[CH:12]=[CH:11][C:10]2[CH2:9][N:8]([C:25]([CH:22]3[CH2:24][CH2:23]3)=[O:26])[CH2:7][CH2:6][C:5]=2[N:4]=1

Participants

6

Reactant 3

HCID 77637Cyclopropanecarbonyl chlorideHCID 81531DiisopropylethylamineHCID 184491652-Chloro-5,6,7,8-tetrahydro-1,6-naphthyridine hydrochloride

Product 1

HCID 582434152-Chloro-6-(cyclopropylcarbonyl)-5,6,7,8-tetrahydro-1,6-naphthyridineYield 105.6%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a room temperature stirred suspension of 2-chloro-5,6,7,8-tetrahydro-1,6-naphthyridine hydrochloride (50 mg, 0.24 mmol) in dichloromethane (2 ml) under a nitrogen atmosphere was added DIPEA (0.12 ml, 0.73 mmol) followed by cyclopropyl carbonyl chloride (24 μl, 0.27 mmol). The resulting mixture was stirred for 16 hours, diluted with dichloromethane (30 ml) and 1M aq. HCl (2 ml). The organic layer was separated and washed with saturated aqueous NaHCO3 (15 ml) and brine (15 ml), dried (MgSO4), filtered and concentrated at reduced pressure to provide the title compound (60 mg, 95%) which was used without further purification.

Workup

  1. stirringThe resulting mixture was stirred for 16 hours
  2. customThe organic layer was separated
  3. washwashed with saturated aqueous NaHCO3 (15 ml) and brine (15 ml)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated at reduced pressure

Sources & evidence

ORD record
ord-0216f6721ccf4d0da782bd4c37e3b266
Source dataset
uspto-grants-2014_04
Patent number
US08691804B2

Reaction notes

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