Isopropyl chloroformate → HCID 58926753, compound

HRID 2378138Notes

Reaction equation

HRID 2378138 reaction equation
COC1N=C2C(=CC=1)N[C@@H](C)C[C@H]2NC(=O)C.[CH2:18]([CH:20]1[CH:29]([CH3:30])[CH:28]([NH:31][C:32]2[CH:33]=[N:34][C:35]3[CH2:36][CH2:37][CH2:38][CH2:39][C:40]=3[CH:41]=2)[C:27]2[N:26]=[C:25]3[CH2:42][CH2:43][CH2:44][CH2:45][C:24]3=[CH:23][C:22]=2[NH:21]1)[CH3:19].Cl[C:47]([O:49][CH:50]([CH3:52])[CH3:51])=[O:48].CN(C1C=CC=CN=1)C>N1C=CC=CC=1>[CH:50]([O:49][C:47]([N:21]1[CH:20]([CH2:18][CH3:19])[CH:29]([CH3:30])[CH:28]([NH:31][C:32]2[CH:33]=[N:34][C:35]3[CH2:36][CH2:37][CH2:38][CH2:39][C:40]=3[CH:41]=2)[C:27]2[N:26]=[C:25]3[CH2:42][CH2:43][CH2:44][CH2:45][C:24]3=[CH:23][C:22]1=2)=[O:48])([CH3:52])[CH3:51]

Participants

6

Reactant 4

HCID 7917Isopropyl chloroformateHCID 218852-DimethylaminopyridineHCID 58926739HCID 58926739, compoundHCID 86760804HCID 86760804, compound

Product 1

HCID 58926753HCID 58926753, 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 (2-ethyl-3-methyl-1,2,3,4,6,7,8,9-octahydro benzo [b][1,5]napthyridin-4yl)-(5,6,7,8-tetrahydro-quinolin-3-yl)-amine (0.575 g, 1.52 mmol), and using isopropyl chloroformate, pyridine, and dimethylaminopyridine. Purify using silica gel column chromatography (gradient eluent, neat ethyl acetate) to provide the title compound (0.218 g, 31%). MS (ES+): 463 (M+H).

Workup

  1. customPurify

Sources & evidence

ORD record
ord-4233abb496e64f19aaec15e750fc2dfa
Source dataset
uspto-grants-2008_12
Patent number
US07470705B2

Reaction notes

Loading…