(4-Methyl-pyridin-2-yl)-(6-oxazol-5-yl-pyridin-2-yl)-amine → N-(2-Hydroxy-ethyl)-N-methyl-3-{5-[6-(4-methyl-pyridin-2-ylamino)-pyridin-2-yl]-oxazol-2-yl}-benzenesulfonamide

HRID 1854596Notes

Reaction equation

HRID 1854596 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([NH:8][C:9]2[N:14]=[C:13]([C:15]3[O:19][C:18](C=CC4C=CC(C#N)=CC=4)=[N:17][CH:16]=3)[CH:12]=[CH:11][CH:10]=2)[CH:3]=1.CC1C=CN=C(NC2C=CC=C(C3OC=NC=3)N=2)C=1.Br[C:50]1[CH:51]=[C:52]([S:56]([N:59]([CH2:61][CH2:62][OH:63])[CH3:60])(=[O:58])=[O:57])[CH:53]=[CH:54][CH:55]=1.O(C(C)(C)C)[Li]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O1CCOCC1>[OH:63][CH2:62][CH2:61][N:59]([CH3:60])[S:56]([C:52]1[CH:53]=[CH:54][CH:55]=[C:50]([C:18]2[O:19][C:15]([C:13]3[CH:12]=[CH:11][CH:10]=[C:9]([NH:8][C:4]4[CH:3]=[C:2]([CH3:1])[CH:7]=[CH:6][N:5]=4)[N:14]=3)=[CH:16][N:17]=2)[CH:51]=1)(=[O:58])=[O:57]

Participants

7

Reactant 4

HCID 53311228(4-Methyl-pyridin-2-yl)-(6-oxazol-5-yl-pyridin-2-yl)-amineHCID 609603403-bromo-N-(2-hydroxy-ethyl)-N-methyl-benzenesulfonamideHCID 673240684-(2-{5-[6-(4-Methyl-pyridin-2-ylamino)-pyridin-2-yl]-oxazol-2-yl}-vinyl)-benzonitrileHCID 178506942HCID 178506942, compound

Product 1

HCID 53312331N-(2-Hydroxy-ethyl)-N-methyl-3-{5-[6-(4-methyl-pyridin-2-ylamino)-pyridin-2-yl]-oxazol-2-yl}-benzenesulfonamideYield 24%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

Prepared as for 4-(2-{5-[6-(4-methyl-pyridin-2-ylamino)-pyridin-2-yl]-oxazol-2-yl}-vinyl)-benzonitrile above using (4-methyl-pyridin-2-yl)-(6-oxazol-5-yl-pyridin-2-yl)-amine, 3-bromo-N-(2-hydroxy-ethyl)-N-methyl-benzenesulfonamide, Pd(PPh3)4, LiOtBu and anhydrous 1,4-dioxane to afford the title compound as a pale yellow solid (24%). 1H NMR (400 MHz, CDCl3) δ 9.81 (s, 1H), 8.45-8.34 (m, 2H), 8.12 (d, J=5.0 Hz, 1H), 8.01-7.77 (m, 5H), 7.66 (d, J=8.4 Hz, 1H), 7.46 (d, J=7.4 Hz, 1H), 6.79 (d, J=5.0 Hz, 1H), 4.83 (t, J=5.5 Hz, 1H), 3.55 (q, J=5.8 Hz, 2H), 3.11 (t, J=5.9 Hz, 2H), 2.81 (d, J=8.0 Hz, 3H), 2.36 (s, 3H). (ESI+) m/z 466 (M+H)+. Retention time=2.45 mins (method 1).

Sources & evidence

ORD record
ord-d726722347914c1aa9873644ad4bf0ac
Source dataset
uspto-grants-2015_02
Patent number
US08962665B2

Reaction notes

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