HCID 90408124, compound → HCID 90409411, compound

HRID 594086Notes

Reaction equation

[CH3:1][N:2]1[CH:7]=[C:6](B2OC(C)(C)C(C)(C)O2)[CH:5]=[C:4]([N:17]2[CH2:22][CH2:21][O:20][CH2:19][CH2:18]2)[C:3]1=[O:23].Br[C:25]1[CH:26]=[C:27]([CH:41]=[CH:42][C:43]=1[CH:44]([F:46])[F:45])[C:28]([NH:30][C:31]1[CH:36]=[CH:35][CH:34]=[C:33]([C:37]([F:40])([F:39])[F:38])[CH:32]=1)=[O:29]>>[F:46][CH:44]([F:45])[C:43]1[CH:25]=[CH:26][C:27]([C:28]([NH:30][C:31]2[CH:36]=[CH:35][CH:34]=[C:33]([C:37]([F:38])([F:39])[F:40])[CH:32]=2)=[O:29])=[CH:41][C:42]=1[C:6]1[CH:5]=[C:4]([N:17]2[CH2:18][CH2:19][O:20][CH2:21][CH2:22]2)[C:3](=[O:23])[N:2]([CH3:1])[CH:7]=1

Participants

Reactant 2

HCID 90408124HCID 90408124, compound

HCID 90409009HCID 90409009, compound

Product 1

HCID 90409411HCID 90409411, compoundYield 8%

Procedure

Step 3: Method 2 was followed using 1-methyl-3-morpholino-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2(1H)-one and 3-bromo-4-(difluoromethyl)-N-(3-(trifluoromethyl)phenyl)benzamide to give 4-(difluoromethyl)-3-(1-methyl-5-morpholino-6-oxo-1,6-dihydropyridin-3-yl)-N-(3-(trifluoromethyl)phenyl)benzamid in 8% yield. LC/MS (m/z)=508.1 (MH+), Rt=0.98 min. 1H NMR (400 MHz, <cd3od>) δ ppm 3.12-3.21 (m, 4H), 3.64 (s, 3H), 3.80-3.90 (m, 4H), 6.96 (d, J=1.96 Hz, 2H), 7.41 (d, J=1.96 Hz, 2H), 7.52-7.62 (m, 1H), 7.84-7.92 (m, 1H), 7.97 (br. s., 2H), 8.05-8.12 (m, 1H), 8.14-8.20 (m, 1H).

Sources & evidence

ORD record: ord-be134d88119449b88587af1c7e7bc85f
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09242969B2

Reaction notes

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