Benzoic Acid → (cis)-Naphthalen-2-ylmethyl 3-(benzoyloxy)-4-(2-(7-(2-methoxyethoxy)imidazo[1,2-a]pyridin-3-yl)quinolin-8-yloxy)piperidine-1-carboxylate

HRID 1095720Notes

Reaction equation

HRID 1095720 reaction equation
[OH:1][C@H:2]1[C@H:7]([O:8][C:9]2[CH:10]=[CH:11][CH:12]=[C:13]3[C:18]=2[N:17]=[C:16]([C:19]2[N:23]4[CH:24]=[CH:25][C:26]([O:28][CH2:29][CH2:30][O:31][CH3:32])=[CH:27][C:22]4=[N:21][CH:20]=2)[CH:15]=[CH:14]3)[CH2:6][CH2:5][N:4]([C:33]([O:35][CH2:36][C:37]2[CH:46]=[CH:45][C:44]3[C:39](=[CH:40][CH:41]=[CH:42][CH:43]=3)[CH:38]=2)=[O:34])[CH2:3]1.[C:47](O)(=[O:54])[C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[C:47]([O:1][C@H:2]1[C@@H:7]([O:8][C:9]2[CH:10]=[CH:11][CH:12]=[C:13]3[C:18]=2[N:17]=[C:16]([C:19]2[N:23]4[CH:24]=[CH:25][C:26]([O:28][CH2:29][CH2:30][O:31][CH3:32])=[CH:27][C:22]4=[N:21][CH:20]=2)[CH:15]=[CH:14]3)[CH2:6][CH2:5][N:4]([C:33]([O:35][CH2:36][C:37]2[CH:46]=[CH:45][C:44]3[C:39](=[CH:40][CH:41]=[CH:42][CH:43]=3)[CH:38]=2)=[O:34])[CH2:3]1)(=[O:54])[C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1

Participants

6

Reactant 4

HCID 243Benzoic AcidHCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 131729513(trans)-Naphthalen-2-ylmethyl 3-hydroxy-4-(2-(7-(2-methoxyethoxy)imidazo[1,2-a]pyridin-3-yl)quinolin-8-yloxy)piperidine-1-carboxylate

Product 1

HCID 131729514(cis)-Naphthalen-2-ylmethyl 3-(benzoyloxy)-4-(2-(7-(2-methoxyethoxy)imidazo[1,2-a]pyridin-3-yl)quinolin-8-yloxy)piperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(trans)-Naphthalen-2-ylmethyl 3-hydroxy-4-(2-(7-(2-methoxyethoxy)imidazo[1,2-a]pyridin-3-yl)quinolin-8-yloxy)piperidine-1-carboxylate (Example 28, Steps A-D; 0.075 g, 0.121 mmol) was dissolved in THF (0.50 mL) and treated with benzoic acid (0.022 g, 0.181 mmol), PPh3 (0.036 g, 0.139 mmol) and diisopropylazodicarboxylate (0.026 ml, 0.133 mmol). The mixture was stirred at ambient temperature for 40 hours, and then the whole reaction mixture was applied to a column of SiO2 and eluted with a gradient from 1-20% (6% NH4OH in MeOH)/ethyl acetate (75 mg). MS ESI (+) m/z 723.2 (M+1) detected.

Workup

  1. customthe whole reaction mixture
  2. washeluted with a gradient from 1-20% (6% NH4OH in MeOH)/ethyl acetate (75 mg)

Sources & evidence

ORD record
ord-58768f9423b74546ace22e05c09c9851
Source dataset
uspto-grants-2012_03
Patent number
US08138181B2

Reaction notes

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