Isopropyl chloroformate → HCID 86613814, compound

HRID 2378136Notes

Reaction equation

HRID 2378136 reaction equation
COC1N=C2C(=CC=1)N[C@@H](C)C[C@H]2NC(=O)C.[CH:18]1([C@H:21]2[CH2:30][C@@H:29]([NH:31][C:32](=[O:34])[CH3:33])[C:28]3[C:23](=[CH:24][CH:25]=[C:26]([C:35]([F:38])([F:37])[F:36])[N:27]=3)[NH:22]2)[CH2:20][CH2:19]1.Cl[C:40]([O:42][CH:43]([CH3:45])[CH3:44])=[O:41].CN(C1C=CC=CN=1)C>N1C=CC=CC=1>[CH:43]([O:42][C:40]([N:22]1[C:23]2[C:28](=[N:27][C:26]([C:35]([F:37])([F:38])[F:36])=[CH:25][CH:24]=2)[C@H:29]([NH:31][C:32](=[O:34])[CH3:33])[CH2:30][C@@H:21]1[CH:18]1[CH2:20][CH2:19]1)=[O:41])([CH3:45])[CH3:44]

Participants

6

Reactant 4

HCID 7917Isopropyl chloroformateHCID 218852-DimethylaminopyridineHCID 86760804HCID 86760804, compoundHCID 86760806HCID 86760806, compound

Product 1

HCID 86613814HCID 86613814, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Prepare the title compound by essentially following the procedure described in Example 46, Step 2, by replacing (+/−)-cis-N-(6-methoxy-2-methyl-1,2,3,4-tetrahydro-[1,5]naphthyridin-4-yl)acetamide, with (+/−)-cis-N-(2-cyclopropyl-6-trifluoromethyl-1,2,3,4-tetrahydro-[1,5]naphthyridin-4-yl)acetamide (1.05 g, 3.512 mmol), and using isopropyl chloroformate, pyridine, and dimethylaminopyridine. Purify using silica gel column chromatography (gradient eluent, 0-5% MeOH in ethyl acetate) to provide the title compound (0.416 g, 31%). MS (ES+): 386 (M+H).

Workup

  1. customPurify

Sources & evidence

ORD record
ord-3daca19b502a46a6a7d29823a2b2cdf1
Source dataset
uspto-grants-2008_12
Patent number
US07470705B2

Reaction notes

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