HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

Triethylamine → Methyl 4-(5-(4-(4-methoxybenzyloxy)-2-(pyridin-2-yl)pyrimidin-5-yl)isoxazol-3-yl)benzoate

HRID 1525340
Notes
Print preview

Reaction equation

HRID 1525340 reaction equation
Cl[C:2](=[N:13][OH:14])[C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][CH:4]=1.[C:15]([C:17]1[C:18]([O:29][CH2:30][C:31]2[CH:36]=[CH:35][C:34]([O:37][CH3:38])=[CH:33][CH:32]=2)=[N:19][C:20]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=2)=[N:21][CH:22]=1)#[CH:16].C(N(CC)CC)C>C1COCC1>[CH3:38][O:37][C:34]1[CH:33]=[CH:32][C:31]([CH2:30][O:29][C:18]2[C:17]([C:15]3[O:14][N:13]=[C:2]([C:3]4[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][CH:4]=4)[CH:16]=3)=[CH:22][N:21]=[C:20]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=3)[N:19]=2)=[CH:36][CH:35]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 73989494alpha-Chloro-4-methoxycarbonylbenzaldoximeHCID 894627915-Ethynyl-4-(4-methoxybenzyloxy)-2-(pyridin-2-yl)pyrimidine

Product 1

HCID 89471307Methyl 4-(5-(4-(4-methoxybenzyloxy)-2-(pyridin-2-yl)pyrimidin-5-yl)isoxazol-3-yl)benzoateYield 38.4%

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent

Procedure

To a mixture of compound 37-e (517 mg, 2.43 mmol), compound 37-j (700 mg, 2.21 mmol) in THF (5 mL) was added triethylamine (335 mg, 3.31 mmol) dropwise. The mixture was stirred overnight at room temperature. The residue obtained from removal of the solvent was purified by flash chromatography (PE:EA=1:2) to afford compound 37-k (420 mg, 38%) as a yellow solid. 1H NMR (300 MHz, CDCl3) δ 8.786 (s, 1H), 8.753-8.731 (d, J=6.6 Hz, 1H), 8.172-8.144 (d, J=8.4 Hz, 2H), 8.004-7.976 (d, J=8.4 Hz, 2H), 7.838-7.806 (m, 1H), 7.645 (s, 1H), 7.615 (s, 1H), 7.495-7.470 (s, 1H), 6.875-6.846 (d, J=8.7 Hz, 2H), 6.697-6.668 (d, J=8.7 Hz, 2H), 5.786 (s, 2H), 3.960 (s, 3H), 3.723 (s, 3H), LC-MS (ESI): 495 [M+H]+.

Workup

  1. customThe residue obtained from removal of the solvent
  2. customwas purified by flash chromatography (PE:EA=1:2)

Sources & evidence

ORD record
ord-e278746d7c894ed1b45d8c5de76fde90
Source dataset
uspto-grants-2015_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09079930B2

Reaction notes

Loading…

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes