Isopropyl chloroformate → HCID 68902103, compound

HRID 2378134Notes

Reaction equation

HRID 2378134 reaction equation
COC1N=C2C(=CC=1)N[C@@H](C)C[C@H]2NC(=O)C.[CH3:18][C@H:19]1[CH2:28][C@@H:27]([NH:29][C:30](=[O:32])[CH3:31])[C:26]2[C:21](=[CH:22][CH:23]=[C:24]([C:33]([F:36])([F:35])[F:34])[N:25]=2)[NH:20]1.Cl[C:38]([O:40][CH:41]([CH3:43])[CH3:42])=[O:39].CN(C1C=CC=CN=1)C>N1C=CC=CC=1>[CH:41]([O:40][C:38]([N:20]1[C:21]2[C:26](=[N:25][C:24]([C:33]([F:34])([F:36])[F:35])=[CH:23][CH:22]=2)[C@H:27]([NH:29][C:30](=[O:32])[CH3:31])[CH2:28][C@@H:19]1[CH3:18])=[O:39])([CH3:43])[CH3:42]

Participants

6

Reactant 4

HCID 7917Isopropyl chloroformateHCID 218852-DimethylaminopyridineHCID 86760804HCID 86760804, compoundHCID 86760805HCID 86760805, compound

Product 1

HCID 68902103HCID 68902103, compoundYield 68%

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-methyl-6-trifluoromethyl-1,2,3,4-tetrahydro-[1,5]naphthyridin-4-yl)acetamide (0.140.g, 0.512 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 (0.123 g, 68%). MS (ES+): 360 (M+H).

Workup

  1. customPurify

Sources & evidence

ORD record
ord-f9297b34248c4f6c94d19511544b39f1
Source dataset
uspto-grants-2008_12
Patent number
US07470705B2

Reaction notes

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