Triethylamine → (S)-2-{[Cinnolin-3-ylmethyl-(7-methoxy-2,2-dimethyl-benzo[1,3]dioxole-5-carbonyl)-amino]-methyl}-pyrrolidine-1-carboxylic acid tert-butyl ester

HRID 2220723Notes

Reaction equation

HRID 2220723 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]([CH:11]=O)[N:2]=1.[C:13]([O:17][C:18]([N:20]1[CH2:24][CH2:23][CH2:22][C@H:21]1[CH2:25][NH2:26])=[O:19])([CH3:16])([CH3:15])[CH3:14].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(N(CC)CC)C.[CH3:48][O:49][C:50]1[C:55]2[O:56][C:57]([CH3:60])([CH3:59])[O:58][C:54]=2[CH:53]=[C:52]([C:61](Cl)=[O:62])[CH:51]=1>ClCCl>[C:13]([O:17][C:18]([N:20]1[CH2:24][CH2:23][CH2:22][C@H:21]1[CH2:25][N:26]([CH2:11][C:3]1[N:2]=[N:1][C:10]2[C:5]([CH:4]=1)=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:61]([C:52]1[CH:51]=[C:50]([O:49][CH3:48])[C:55]2[O:56][C:57]([CH3:60])([CH3:59])[O:58][C:54]=2[CH:53]=1)=[O:62])=[O:19])([CH3:16])([CH3:15])[CH3:14]

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 1512533tert-Butyl (2S)-2-(aminomethyl)pyrrolidine-1-carboxylateHCID 5049666Sodium triacetoxyborohydrideHCID 17859657Cinnoline-3-carbaldehydeHCID 714100777-Methoxy-2,2-dimethyl-2H-1,3-benzodioxole-5-carbonyl chloride

Product 1

HCID 58622200(S)-2-{[Cinnolin-3-ylmethyl-(7-methoxy-2,2-dimethyl-benzo[1,3]dioxole-5-carbonyl)-amino]-methyl}-pyrrolidine-1-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Experimental conditions analogous to Example 1, from 0.26 g (1.65 mmol) of cinnoline-3-carbaldehyde, 0.49 g (2.47 mmol) of (S)-2-aminomethyl-pyrrolidine-1-carboxylic acid tert-butyl ester, 10 mL dichloromethane, and 0.52 mg (2.47 mmol) of sodium triacetoxyborohydride. The reaction was quenched with aqueous sodium bicarbonate. The residue from the organic layer was purified using flash chromatography (0-20% methanol in dichloromethane). The organic layer was concentrated under vacuum and dissolved in 5 mL dichloromethane. To this solution were added 0.34 mL (2.47 mmol) of triethylamine and 0.4 g (1.65 mmol) of 7-methoxy-2,2-dimethyl-benzo[1,3]dioxole-5-carbonyl chloride. After 1 hour the reaction mixture was purified using flash chromatography (10-100% ethyl acetate in hexane), gave 182 mg as a yellow solid. LC-MSD, m/z for C30H36N4O6 [M+H]+: 549.7

Workup

  1. customThe reaction was quenched with aqueous sodium bicarbonate
  2. customThe residue from the organic layer was purified
  3. concentrationThe organic layer was concentrated under vacuum
  4. dissolutiondissolved in 5 mL dichloromethane
  5. customAfter 1 hour the reaction mixture was purified
  6. customgave 182 mg as a yellow solid

Sources & evidence

ORD record
ord-f594212ef5e64836bd6738dbbdbd105b
Source dataset
uspto-grants-2008_08
Patent number
US07417062B2

Reaction notes

Loading…