Methanol → methyl 6-(4-(3,5-dichloropyridin-4-ylamino)-7-methoxy-2-oxo-2H-chromen-8-yloxy)hexanoate

HRID 20680Notes

Reaction equation

HRID 20680 reaction equation
[Si](C=[N+]=[N-])(C)(C)[CH3:2].[Cl:8][C:9]1[CH:10]=[N:11][CH:12]=[C:13]([Cl:38])[C:14]=1[NH:15][C:16]1[C:25]2[C:20](=[C:21]([O:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][C:34]([OH:36])=[O:35])[C:22]([O:26][CH3:27])=[CH:23][CH:24]=2)[O:19][C:18](=[O:37])[CH:17]=1.CO>C1(C)C=CC=CC=1>[Cl:8][C:9]1[CH:10]=[N:11][CH:12]=[C:13]([Cl:38])[C:14]=1[NH:15][C:16]1[C:25]2[C:20](=[C:21]([O:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][C:34]([O:36][CH3:2])=[O:35])[C:22]([O:26][CH3:27])=[CH:23][CH:24]=2)[O:19][C:18](=[O:37])[CH:17]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 167693TrimethylsilyldiazomethaneHCID 248497096-(4-(3,5-dichloropyridin-4-ylamino)-7-methoxy-2-oxo-2H-chromen-8-yloxy)hexanoic acid

Product 1

HCID 24849802methyl 6-(4-(3,5-dichloropyridin-4-ylamino)-7-methoxy-2-oxo-2H-chromen-8-yloxy)hexanoate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of TMSCHN2 (0.75 mL, 2M Et2O, 1.5 mmol) was added to a solution of 6-(4-(3,5-dichloropyridin-4-ylamino)-7-methoxy-2-oxo-2H-chromen-8-yloxy)hexanoic acid (115 mg, 0.25 mmol, Example 44), methanol (1 mL), and toluene (8 mL). After 10 min, the reaction was concentrated and purified by silica gel chromatography (4:1→1:4; hexanes:ethyl acetate) to give methyl 6-(4-(3,5-dichloropyridin-4-ylamino)-7-methoxy-2-oxo-2H-chromen-8-yloxy)hexanoate: 1H NMR (400 MHz, DMSO-d6): δ 9.50 (s, 1H), 8.81 (s, 2H), 7.94 (d, 1H), 7.20 (d, 1H), 4.63 (s, 1H), 3.97 (t, 2H), 3.91 (s, 3H), 3.56 (s, 3H), 2.31 (t, 2H), 1.67 (m, 2H), 1.57 (m, 2H), 1.46 (m, 2H); MS (ESI): 480.9.

Workup

  1. concentrationthe reaction was concentrated
  2. custompurified by silica gel chromatography (4:1→1:4; hexanes:ethyl acetate)

Sources & evidence

ORD record
ord-445fc7e00a7a4d09a39e0ac587914b1d
Source dataset
uspto-grants-2010_06
Patent number
US07745646B2

Reaction notes

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