N-Cyclopropyl-N'-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)urea → (S)-1-cyclopropyl-3-(4-(6-(5-fluoro-2-(methylsulfonyl)phenyl)-2-(3-methylmorpholino)pyrimidin-4-yl)phenyl)urea

HRID 1771554Notes

Reaction equation

HRID 1771554 reaction equation
FC1C=C(C2N=C(SC)N=C(N3CCOC[C@@H]3C)C=2)C=NC=1.Cl[C:24]1[CH:29]=[C:28]([C:30]2[CH:35]=[C:34]([F:36])[CH:33]=[CH:32][C:31]=2[S:37]([CH3:40])(=[O:39])=[O:38])[N:27]=[C:26]([N:41]2[CH2:46][CH2:45][O:44][CH2:43][C@@H:42]2[CH3:47])[N:25]=1.[CH:48]1([NH:51][C:52](=[O:69])[NH:53][C:54]2[CH:59]=[CH:58][C:57](B3OC(C)(C)C(C)(C)O3)=[CH:56][CH:55]=2)[CH2:50][CH2:49]1>>[CH:48]1([NH:51][C:52]([NH:53][C:54]2[CH:59]=[CH:58][C:57]([C:24]3[CH:29]=[C:28]([C:30]4[CH:35]=[C:34]([F:36])[CH:33]=[CH:32][C:31]=4[S:37]([CH3:40])(=[O:39])=[O:38])[N:27]=[C:26]([N:41]4[CH2:46][CH2:45][O:44][CH2:43][C@@H:42]4[CH3:47])[N:25]=3)=[CH:56][CH:55]=2)=[O:69])[CH2:50][CH2:49]1

Participants

4

Reactant 3

HCID 44119149N-Cyclopropyl-N'-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ureaHCID 67382782(S)-4-(6-(5-fluoropyridin-3-yl)-2-(methylthio)pyrimidin-4-yl)-3-methylmorpholineHCID 86691148(S)-4-(4-chloro-6-(5-fluoro-2-(methylsulfonyl)phenyl)pyrimidin-2-yl)-3-methylmorpholine2×

Product 1

HCID 53380861(S)-1-cyclopropyl-3-(4-(6-(5-fluoro-2-(methylsulfonyl)phenyl)-2-(3-methylmorpholino)pyrimidin-4-yl)phenyl)urea

Procedure

Method as described for intermediate 5 using (S)-4-(4-chloro-6-(5-fluoro-2-(methylsulfonyl)phenyl)pyrimidin-2-yl)-3-methylmorpholine (intermediate 16) and 4-(3-cyclopropylureido)phenyl boronic acid pinacol ester. Material was purified by prep HPLC (low pH) to afford a brown solid, (43 mg, 17%).

Workup

  1. customMaterial was purified by prep HPLC (low pH)
  2. customto afford a brown solid, (43 mg, 17%)

Sources & evidence

ORD record
ord-5f536a918673430aaf859641dfe80013
Source dataset
uspto-grants-2016_02
Patent number
US09249129B2

Reaction notes

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