Ethanesulfonamide → US10023592, Example 173

HRID 575662Notes

Reaction equation

HRID 575662 reaction equation
ClC1C(OC2C=CC(F)=CC=2F)=CN=C(S(C)(=O)=O)N=1.CN1C=C(B2OC(C)(C)C(C)(C)O2)C2CCCCC=2C1=O.[F:42][C:43]1[CH:71]=[C:70]([F:72])[CH:69]=[CH:68][C:44]=1[O:45][C:46]1[C:47]([C:56]2[C:65]3[CH2:64][CH2:63][CH2:62][CH2:61][C:60]=3[C:59](=[O:66])[N:58]([CH3:67])[CH:57]=2)=[N:48][C:49](S(C)(=O)=O)=[N:50][CH:51]=1.[CH2:73]([S:75]([NH2:78])(=[O:77])=[O:76])[CH3:74]>>[F:42][C:43]1[CH:71]=[C:70]([F:72])[CH:69]=[CH:68][C:44]=1[O:45][C:46]1[C:47]([C:56]2[C:65]3[CH2:64][CH2:63][CH2:62][CH2:61][C:60]=3[C:59](=[O:66])[N:58]([CH3:67])[CH:57]=2)=[N:48][C:49]([NH:78][S:75]([CH2:73][CH3:74])(=[O:77])=[O:76])=[N:50][CH:51]=1

Participants

5

Reactant 4

HCID 73702EthanesulfonamideHCID 1180213754-[5-(2,4-Difluorophenoxy)-2-methylsulfonylpyrimidin-4-yl]-2-methyl-5,6,7,8-tetrahydroisoquinolin-1-oneHCID 1180215444-Chloro-5-(2,4-difluorophenoxy)-2-methylsulfonylpyrimidineHCID 1238019002-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5,6,7,8-tetrahydroisoquinolin-1-one

Product 1

HCID 118021925US10023592, Example 173

Procedure

The title compound of Example 149, step 3 was reacted with the title compound of Example 163, step 3 in a manner similar to Example 163, step 4 and the resulting 4-[5-(2,4-difluorophenoxy)-2-methylsulfonylpyrimidin-4-yl]-2-methyl-5,6,7,8-tetrahydroisoquinolin-1-one was treated with EtSO2NH2 instead of MeSO2NH2 in a manner similar to Example 163, step 5 to give the title compound. 1H NMR (DMSO-d6, 400 MHz): δ 8.38 (s, 1H), 7.61 (s, 1H), 7.35-7.31 (m, 1H), 7.04-6.95 (m, 2H), 3.41 (s, 3H), 3.30-3.20 (m, 2H), 2.42-2.40 (m, 2H), 2.32-2.30 (m, 2H), 1.61-1.51 (m, 4H), 1.18 (t, J=7.2 Hz, 3H). LCMS: 477.1 (M+H)+

Sources & evidence

ORD record
ord-4411efb1ea544bc391594d753e5bda26
Source dataset
uspto-grants-2015_05
Patent number
US09034900B2

Reaction notes

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