US10023592, Example 238 → US10023592, Example 241

HRID 575714Notes

Reaction equation

HRID 575714 reaction equation
C1(COC2C=CC(S(C)(=O)=O)=CC=2[C:16]2[C:17]3[O:26][C:25]([CH3:27])=[N:24][C:18]=3[C:19](=[O:23])[N:20]([CH3:22])[CH:21]=2)CC1.[F:28][C:29]1[CH:56]=[C:55]([F:57])[CH:54]=[CH:53][C:30]=1[O:31][C:32]1[CH:37]=[CH:36][C:35]([NH:38][S:39]([CH2:42][CH3:43])(=[O:41])=[O:40])=[CH:34][C:33]=1B1OC(C)(C)C(C)(C)O1>>[F:28][C:29]1[CH:56]=[C:55]([F:57])[CH:54]=[CH:53][C:30]=1[O:31][C:32]1[CH:37]=[CH:36][C:35]([NH:38][S:39]([CH2:42][CH3:43])(=[O:40])=[O:41])=[CH:34][C:33]=1[C:16]1[C:17]2[O:26][C:25]([CH3:27])=[N:24][C:18]=2[C:19](=[O:23])[N:20]([CH3:22])[CH:21]=1

Participants

3

Reactant 2

HCID 118021440US10023592, Example 238HCID 124081953N-(4-(2,4-difluorophenoxy)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ethanesulfonamide

Product 1

HCID 118021644US10023592, Example 241

Procedure

7-bromo-2,5-dimethyl-[1,3]oxazolo[4,5-c]pyridin-4-one prepared in Example 238 and N-[4-(2,4-difluorophenoxy)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]ethanesulfonamide prepared in Example 240 were reacted in a manner similar to Example 237, step 6 to give the title compound. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.23 (t, J=6.95 Hz, 3H) 2.45 (s, 3H) 3.13 (d, J=7.83 Hz, 2H) 3.58 (s, 3H) 6.95 (d, J=8.59 Hz, 1H) 7.03-7.30 (m, 3H) 7.30-7.48 (m, 2H) 7.91 (s, 1H) 9.86 (s, 1H). LCMS: 476 (M+H)+

Sources & evidence

ORD record
ord-c3a2dbdb82b84f9fb0c997402da1054f
Source dataset
uspto-grants-2015_05
Patent number
US09034900B2

Reaction notes

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