Cyclopentylmethyl 4-methylbenzene-1-sulfonate → 8-(Cyclopentylmethoxy)-4-(3,5-dichloropyridin-4-ylamino)-7-methoxy-2H-chromen-2-one

HRID 20664Notes

Reaction equation

HRID 20664 reaction equation
CC1C=CC(S([O:11][CH2:12][CH:13]2[CH2:17][CH2:16][CH2:15][CH2:14]2)(=O)=O)=CC=1.[Cl:18][C:19]1[CH:20]=[N:21][CH:22]=[C:23]([Cl:40])[C:24]=1[NH:25][C:26]1[C:35]2[C:30](=[C:31](O)[C:32]([O:36][CH3:37])=[CH:33][CH:34]=2)[O:29][C:28](=[O:39])[CH:27]=1>>[CH:13]1([CH2:12][O:11][C:31]2[C:32]([O:36][CH3:37])=[CH:33][CH:34]=[C:35]3[C:30]=2[O:29][C:28](=[O:39])[CH:27]=[C:26]3[NH:25][C:24]2[C:23]([Cl:40])=[CH:22][N:21]=[CH:20][C:19]=2[Cl:18])[CH2:14][CH2:15][CH2:16][CH2:17]1

Participants

3

Reactant 2

HCID 12568544Cyclopentylmethyl 4-methylbenzene-1-sulfonateHCID 248495704-(3,5-dichloropyridin-4-ylamino)-8-hydroxy-7-methoxy-2H-chromen-2-one

Product 1

HCID 248496668-(Cyclopentylmethoxy)-4-(3,5-dichloropyridin-4-ylamino)-7-methoxy-2H-chromen-2-one

Procedure

The title compound was prepared from cyclopentylmethyl 4-methylbenzenesulfonate and 4-(3,5-dichloropyridin-4-ylamino)-8-hydroxy-7-methoxy-2H-chromen-2-one (Example 29) following the procedure outlined in Example 25. 1H NMR (400 MHz, DMSO-d6): δ 9.51 (s, 1H), 8.81 (s, 2H), 7.93 (d, 1H), 7.20 (d, 1H), 4.64 (s, 1H), 3.91 (s, 3H), 3.84 (d, 2H), 2.28 (m, 1H), 1.80-1.35 (m, 8H); MS (ESI): 434.9.

Sources & evidence

ORD record
ord-c23a01cce2e04beab5feffd6df782fa6
Source dataset
uspto-grants-2010_06
Patent number
US07745646B2

Reaction notes

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