Diisopropylethylamine → phenylmethyl[((3S)-1-{2-[3-chloro-6-(methyloxy)-1,5-naphthyridin-4-yl]ethyl}-3-pyrrolidinyl)methyl]carbamate

HRID 639071Notes

Reaction equation

HRID 639071 reaction equation
[Cl:1][C:2]1[C:11]([CH:12]=[CH2:13])=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([O:14][CH3:15])=[N:9]2)=[N:4][CH:3]=1.Cl.C1(C[N:24]([CH2:28][C@@H:29]2[CH2:33][CH2:32][NH:31][CH2:30]2)[C:25](=[O:27])[OH:26])C=CC=CC=1.C(N([CH:40]([CH3:42])[CH3:41])CC)(C)C>CN(C=O)C>[C:40]1([CH2:41][O:26][C:25](=[O:27])[NH:24][CH2:28][C@@H:29]2[CH2:33][CH2:32][N:31]([CH2:13][CH2:12][C:11]3[C:10]4[C:5](=[CH:6][CH:7]=[C:8]([O:14][CH3:15])[N:9]=4)[N:4]=[CH:3][C:2]=3[Cl:1])[CH2:30]2)[CH:42]=[CH:10][CH:11]=[CH:2][CH:3]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 592543637-Chloro-2-methoxy-8-vinyl-[1,5]naphthyridineHCID 68576786Phenylmethyl[(3r)-3-pyrrolidinylmethyl]carbamate hydrochloride

Product 1

HCID 59026200phenylmethyl[((3S)-1-{2-[3-chloro-6-(methyloxy)-1,5-naphthyridin-4-yl]ethyl}-3-pyrrolidinyl)methyl]carbamateYield 75.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 7-chloro-8-ethenyl-2-(methyloxy)-1,5-naphthyridine (1.68 g, 7.6 mmol) in DMF (5 mL) was added phenylmethyl[(3R)-3-pyrrolidinylmethyl]carbamate hydrochloride (2.1 g, 7.6 mmol) and diisopropylethylamine (3.9 mL, 22.8 mmol)). The reaction was heated at 100° C. for 18 h. Upon cooling to room temperature, the crude reaction mixture was directly added to a silica gel column and purified to give a light brown oil (1.3 g): LC/MS (ES) m/e 455 (M+H)+.

Workup

  1. temperatureUpon cooling to room temperature
  2. customthe crude reaction mixture
  3. additionwas directly added to a silica gel column
  4. custompurified

Sources & evidence

ORD record
ord-78e6a57418fb42008d31ec9beaa5e5f3
Source dataset
uspto-grants-2010_04
Patent number
US07691850B2

Reaction notes

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