6-[2-(2,4-Difluorophenyl)chroman-6-yloxy]-pyridin-3-ylamine → N-{6-[2-(2,4-difluorophenyl)chroman-6-yloxy]pyridin-3-yl}methane sulfonamide

HRID 31283Notes

Reaction equation

HRID 31283 reaction equation
C1(C2CCC3C(=CC=C(OC4N=CC(N[S:25]([CH3:28])(=[O:27])=[O:26])=CC=4)C=3)O2)C=CC=CC=1.[F:29][C:30]1[CH:35]=[C:34]([F:36])[CH:33]=[CH:32][C:31]=1[CH:37]1[CH2:46][CH2:45][C:44]2[C:39](=[CH:40][CH:41]=[C:42]([O:47][C:48]3[N:53]=[CH:52][C:51]([NH2:54])=[CH:50][CH:49]=3)[CH:43]=2)[O:38]1>>[F:29][C:30]1[CH:35]=[C:34]([F:36])[CH:33]=[CH:32][C:31]=1[CH:37]1[CH2:46][CH2:45][C:44]2[C:39](=[CH:40][CH:41]=[C:42]([O:47][C:48]3[N:53]=[CH:52][C:51]([NH:54][S:25]([CH3:28])(=[O:27])=[O:26])=[CH:50][CH:49]=3)[CH:43]=2)[O:38]1

Participants

3

Reactant 2

HCID 179784706-[2-(2,4-Difluorophenyl)chroman-6-yloxy]-pyridin-3-ylamineHCID 17978472N-[6-(2-phenylchroman-6-yloxy)pyridin-3-yl]methanesulfonamide

Product 1

HCID 17978551N-{6-[2-(2,4-difluorophenyl)chroman-6-yloxy]pyridin-3-yl}methane sulfonamide

Procedure

N-{6-[2-(2,4-difluorophenyl)chroman-6-yloxy]pyridin-3-yl}methane sulfonamide was prepared as described for N-[6-(2-phenylchroman-6-yloxy)pyridin-3-yl]methane sulfonamide in Example 46 starting from 100 mg of 6-[2-(2,4-difluorophenyl)chroman-6-yloxy]-pyridin-3-ylamine (Example 70). The product was crystallised from a mixture of methanol and diethyl ether. 1H NMR (400 MHz, d6-DMSO) δ: 9.67 (s, 1H), 7.99 (d, 1H, J 2.8 Hz), 7.67 (dd, 1H, J 8.8, 2.8 Hz), 7.60 (m, 1H), 7.30 (m, 1H), 7.16 (m, 1H), 6.98 (d, 1H, J 8.8 Hz), 6.92-6.86 (m, 3H), 5.31 (dd, 1H, J 10.3, 2.3 Hz), 3.01 (m, 1H), 2.98 (s, 3H), 2.76 (m, 1H), 2.16 (m, 1H), 2.06 (m, 1H).

Workup

  1. customThe product was crystallised from a mixture of methanol and diethyl ether

Sources & evidence

ORD record
ord-25846f1e22ff474d934070f01cc4ff25
Source dataset
uspto-grants-2008_09
Patent number
US07425568B2

Reaction notes

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