Water → 4-(3,5-dichloropyridin-4-ylamino)-8-(((2S,3R,4S)-3,4-dihydroxy-5-oxotetrahydrofuran-2-yl)methoxy)-7-methoxy-2H-chromen-2-one

HRID 20673Notes

Reaction equation

HRID 20673 reaction equation
FC(F)(F)C(O)=O.[Cl:8][C:9]1[CH:10]=[N:11][CH:12]=[C:13]([Cl:42])[C:14]=1[NH:15][C:16]1[C:25]2[C:20](=[C:21]([O:28][CH2:29][C@H:30]3[C@H:37]4[C@H:33]([O:34]C(C)(C)[O:36]4)[C:32](=[O:40])[O:31]3)[C:22]([O:26][CH3:27])=[CH:23][CH:24]=2)[O:19][C:18](=[O:41])[CH:17]=1.O>C1COCC1>[Cl:8][C:9]1[CH:10]=[N:11][CH:12]=[C:13]([Cl:42])[C:14]=1[NH:15][C:16]1[C:25]2[C:20](=[C:21]([O:28][CH2:29][C@H:30]3[C@H:37]([OH:36])[C@H:33]([OH:34])[C:32](=[O:40])[O:31]3)[C:22]([O:26][CH3:27])=[CH:23][CH:24]=2)[O:19][C:18](=[O:41])[CH:17]=1

Participants

5

Reactant 3

HCID 962WaterHCID 6422Trifluoroacetic acid2×HCID 248497564-(3,5-Dichloropyridin-4-ylamino)-8-(((3aS,4S,6aS)-2,2-dimethyl-6-oxotetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methoxy)-7-methoxy-2H-chromen-2-one

Product 1

HCID 248497574-(3,5-dichloropyridin-4-ylamino)-8-(((2S,3R,4S)-3,4-dihydroxy-5-oxotetrahydrofuran-2-yl)methoxy)-7-methoxy-2H-chromen-2-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Trifluoroacetic acid (0.1 mL) was added to a mixture of 4-(3,5-dichloropyridin-4-ylamino)-8-(((3aS,4S,6aS)-2,2-dimethyl-6-oxotetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methoxy)-7-methoxy-2H-chromen-2-one (60 mg, 0.12 mmol, Example 50), water (0.1 mL), and THF (3 mL). The mixture was stirred at rt for 2 d. Then, more trifluoroacetic acid (3 mL) was added over time until the reaction was complete by LCMS. The mixture was concentrated to give 4-(3,5-dichloropyridin-4-ylamino)-8-(((2S,3R,4S)-3,4-dihydroxy-5-oxotetrahydrofuran-2-yl)methoxy)-7-methoxy-2H-chromen-2-one: 1H NMR (400 MHz, DMSO-d6): δ 9.55 (s, 1H), 8.81 (s, 2H), 7.97 (d, 1H), 7.21 (d, 1H), 5.74 (s, 1H), 4.63 (s, 1H), 4.61 (d, 1H), 4.49 (m, 1H), 4.42 (d, 1H), 4.23 (d, 1H), 3.91 (s, 3H); MS (ESI): 482.8.

Workup

  1. concentrationThe mixture was concentrated

Sources & evidence

ORD record
ord-9ba8d1009ba54f179fe1cfec193065ee
Source dataset
uspto-grants-2010_06
Patent number
US07745646B2

Reaction notes

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