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

HRID 1771573Notes

Reaction equation

HRID 1771573 reaction equation
FC1C=C(C2N=C(SC)N=C(N3CCOC[C@@H]3C)C=2)C=NC=1.Cl[C:24]1[N:29]=[C:28]([N:30]2[CH2:35][CH2:34][O:33][CH2:32][C@@H:31]2[CH3:36])[CH:27]=[C:26]([C:37]2[CH:42]=[C:41]([F:43])[CH:40]=[CH:39][C:38]=2[S:44]([CH3:47])(=[O:46])=[O:45])[N:25]=1.[CH:48]1([NH:51][C:52]([NH:54][C:55]2[CH:60]=[CH:59][C:58](B3OC(C)(C)C(C)(C)O3)=[C:57]([F:70])[CH:56]=2)=[O:53])[CH2:50][CH2:49]1>>[CH:48]1([NH:51][C:52]([NH:54][C:55]2[CH:60]=[CH:59][C:58]([C:24]3[N:25]=[C:26]([C:37]4[CH:42]=[C:41]([F:43])[CH:40]=[CH:39][C:38]=4[S:44]([CH3:47])(=[O:46])=[O:45])[CH:27]=[C:28]([N:30]4[CH2:35][CH2:34][O:33][CH2:32][C@@H:31]4[CH3:36])[N:29]=3)=[C:57]([F:70])[CH:56]=2)=[O:53])[CH2:50][CH2:49]1

Participants

4

Reactant 3

HCID 666792291-Cyclopropyl-3-(3-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)urea2×HCID 67382782(S)-4-(6-(5-fluoropyridin-3-yl)-2-(methylthio)pyrimidin-4-yl)-3-methylmorpholineHCID 86691149(S)-4-(2-chloro-6-(5-fluoro-2-(methylsulfonyl)phenyl)pyrimidin-4-yl)-3-methylmorpholine2×

Product 1

HCID 53379772(S)-1-cyclopropyl-3-(3-fluoro-4-(4-(5-fluoro-2-(methylsulfonyl)phenyl)-6-(3-methylmorpholino)pyrimidin-2-yl)phenyl)urea

Procedure

Method as described for intermediate 5 using (S)-4-(2-chloro-6-(5-fluoro-2-(methylsulfonyl)phenyl)pyrimidin-4-yl)-3-methylmorpholine (intermediate 10) and 1-cyclopropyl-3-(3-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)urea (intermediate 11). Material was purified by prep HPLC (low pH) to afford a brown gum, (70 mg, 47%).

Workup

  1. customMaterial was purified by prep HPLC (low pH)
  2. customto afford a brown gum, (70 mg, 47%)

Sources & evidence

ORD record
ord-80298e89975a4419afe26f54c2dc7c03
Source dataset
uspto-grants-2016_02
Patent number
US09249129B2

Reaction notes

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