(S)-tert-butyl 3-(2-bromo-N-methylphenylsulfonamido)-piperidine-1-carboxylate → 4'-(2-Aminopyrimidin-5-yl)-3'-fluoro-N-methyl-N-[(3S)-piperidin-3-yl]biphenyl-2-sulfonamide

HRID 1523869Notes

Reaction equation

HRID 1523869 reaction equation
[F:1][C:2]1[CH:7]=[C:6](B2OC(C)(C)C(C)(C)O2)[CH:5]=[CH:4][C:3]=1[C:17]1[CH:18]=[N:19][C:20]([NH2:23])=[N:21][CH:22]=1.Br[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[S:31]([N:34]([C@H:36]1[CH2:41][CH2:40][CH2:39][N:38](C(OC(C)(C)C)=O)[CH2:37]1)[CH3:35])(=[O:33])=[O:32]>>[NH2:23][C:20]1[N:21]=[CH:22][C:17]([C:3]2[CH:4]=[CH:5][C:6]([C:25]3[C:26]([S:31]([N:34]([CH3:35])[C@H:36]4[CH2:41][CH2:40][CH2:39][NH:38][CH2:37]4)(=[O:33])=[O:32])=[CH:27][CH:28]=[CH:29][CH:30]=3)=[CH:7][C:2]=2[F:1])=[CH:18][N:19]=1

Participants

3

Reactant 2

HCID 90312865(S)-tert-butyl 3-(2-bromo-N-methylphenylsulfonamido)-piperidine-1-carboxylateHCID 903131425-(2-Fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyrimidin-2-amine

Product 1

HCID 903140174'-(2-Aminopyrimidin-5-yl)-3'-fluoro-N-methyl-N-[(3S)-piperidin-3-yl]biphenyl-2-sulfonamide

Procedure

The title compound was prepared using methods analogous to those described in Example 376 using 5-(2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyrimidin-2-amine and (S)-tert-butyl 3-(2-bromo-N-methylphenylsulfonamido)-piperidine-1-carboxylate yielding 41 mg (48%) of the title compound after HPLC purification. MS (ESI): mass calcd. for C27H32FN5O4S, 541.21; m/z found, 542.1 [M+H]+.

Workup

  1. customThe title compound was prepared
  2. customafter HPLC purification

Sources & evidence

ORD record
ord-bf1d127f428e473f84804b5d623e70e8
Source dataset
uspto-grants-2015_07
Patent number
US09079866B2

Reaction notes

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