(1-Aminocyclobutyl)methanol → (S)-1-(4-(6-(5-fluoro-2-(methylsulfonyl)phenyl)-2-(3-methylmorpholino)pyrimidin-4-yl)phenyl)-3-(1-(hydroxymethyl)cyclobutyl)urea

HRID 1771582Notes

Reaction equation

HRID 1771582 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:42]1([CH2:46][OH:47])[CH2:45][CH2:44][CH2:43]1>>[F:28][C:26]1[CH:25]=[CH:24][C:23]([S:29]([CH3:32])(=[O:30])=[O:31])=[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:14]=[CH:15][C:10]([NH:9][C:8]([NH:41][C:42]4([CH2:46][OH:47])[CH2:45][CH2:44][CH2:43]4)=[O:40])=[CH:11][CH:12]=3)[CH:21]=2)[CH:27]=1

Participants

3

Reactant 2

HCID 21624254(1-Aminocyclobutyl)methanolHCID 89717157(S)-phenyl(4-(6-(5-fluoro-2-(methylsulfonyl)phenyl)-2-(3-methylmorpholino)pyrimidin-4-yl)phenyl)carbamate

Product 1

HCID 67382639(S)-1-(4-(6-(5-fluoro-2-(methylsulfonyl)phenyl)-2-(3-methylmorpholino)pyrimidin-4-yl)phenyl)-3-(1-(hydroxymethyl)cyclobutyl)urea

Procedure

Method as described for example 58 using intermediate 32 (100 mg, 0.18 mmol) and (1-aminocyclobutyl)methanol (27 mg, 0.267 mmol). The reaction mixture was purified by prep HPLC at low pH to afford the title compound. (54 mg, 53%)

Workup

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

Sources & evidence

ORD record
ord-b183e44792664993bcd2fc41ab1b756e
Source dataset
uspto-grants-2016_02
Patent number
US09249129B2

Reaction notes

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