Acetic Acid → (+/-)9-{6-[(4-Methoxy-benzyl)-methyl-amino]-pyridin-2-yl}-3-quinoxalin-2-yl-nonanoic acid ethyl ester

HRID 860085Notes

Reaction equation

[CH2:1]([O:3][C:4](=[O:39])[CH2:5][CH:6]([C:29]1[CH:38]=[N:37][C:36]2[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=2)[N:30]=1)[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([NH:19][CH2:20][C:21]2[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=2)[N:14]=1)[CH3:2].C=O.[C:42](O)(=O)C.[BH3-]C#N.[Na+]>CO>[CH2:1]([O:3][C:4](=[O:39])[CH2:5][CH:6]([C:29]1[CH:38]=[N:37][C:36]2[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=2)[N:30]=1)[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([N:19]([CH2:20][C:21]2[CH:22]=[CH:23][C:24]([O:27][CH3:28])=[CH:25][CH:26]=2)[CH3:42])[N:14]=1)[CH3:2]

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of 22-5 (0.130 g, 0.246 mmol) in methanol (5 mL) was added paraformaldehyde (0.07 g) and acetic acid (0.071 mL, 1.23 mmol). After stirring at 50° C. for 15 minutes, NaCNBH3 (0.020 g, 0.32 mmol) was added. After stirring 2 hours the solution was concentrated in vacuo. The residue was dissolved in CHCl3 (125 mL) and washed with saturated NaHCO3, dried, and concentrated to afford 22-6 (0.132 g).

Workup

stirringAfter stirring 2 hours the solution
concentrationwas concentrated in vacuo
dissolutionThe residue was dissolved in CHCl3 (125 mL)
washwashed with saturated NaHCO3
customdried
concentrationconcentrated

Sources & evidence

ORD record: ord-d47eedc5015440119ef69f886fdc4761
Source dataset: uspto-grants-2006_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07153862B2

Reaction notes

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