(R)-(-)-2-Amino-1-propanol → 1-(4-(6-(5-fluoro-2-(methylsulfonyl)phenyl)-2-((S)-3-methylmorpholino)pyrimidin-4-yl)phenyl)-3-((R)-1-hydroxypropan-2-yl)urea

HRID 1771580Notes

Reaction equation

HRID 1771580 reaction equation
C1(O[C:8](=[O:40])[NH:9][C:10]2[CH:15]=[CH:14][C:13]([C:16]3[CH:21]=[C:20]([C:22]4[CH:27]=[C:26]([F:28])[CH:25]=[CH:24][C:23]=4[S:29]([CH3:32])(=[O:31])=[O:30])[N:19]=[C:18]([N:33]4[CH2:38][CH2:37][O:36][CH2:35][C@@H:34]4[CH3:39])[N:17]=3)=[CH:12][CH:11]=2)C=CC=CC=1.[NH2:41][C@H:42]([CH3:45])[CH2:43][OH:44]>>[F:28][C:26]1[CH:25]=[CH:24][C:23]([S:29]([CH3:32])(=[O:31])=[O:30])=[C:22]([C:20]2[N:19]=[C:18]([N:33]3[CH2:38][CH2:37][O:36][CH2:35][C@@H:34]3[CH3:39])[N:17]=[C:16]([C:13]3[CH:12]=[CH:11][C:10]([NH:9][C:8]([NH:41][C@H:42]([CH3:45])[CH2:43][OH:44])=[O:40])=[CH:15][CH:14]=3)[CH:21]=2)[CH:27]=1

Participants

3

Reactant 2

HCID 80308(R)-(-)-2-Amino-1-propanolHCID 89717157(S)-phenyl(4-(6-(5-fluoro-2-(methylsulfonyl)phenyl)-2-(3-methylmorpholino)pyrimidin-4-yl)phenyl)carbamate

Product 1

HCID 673824131-(4-(6-(5-fluoro-2-(methylsulfonyl)phenyl)-2-((S)-3-methylmorpholino)pyrimidin-4-yl)phenyl)-3-((R)-1-hydroxypropan-2-yl)urea

Procedure

Method as described for example 58 using intermediate 32 (100 mg, 0.18 mmol) and (R)-2-aminopropan-1-ol (20 mg, 0.267 mmol). The reaction mixture was purified by prep HPLC at low pH to afford the title compound. (59 mg, 61%)

Workup

  1. customThe reaction mixture was purified by prep HPLC at low pH

Sources & evidence

ORD record
ord-2c848ca1cf744f8ab617c74021e59b4e
Source dataset
uspto-grants-2016_02
Patent number
US09249129B2

Reaction notes

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