Aminoacetonitrile → HCID 86594560, compound

HRID 1744095Notes

Reaction equation

HRID 1744095 reaction equation
NCC#N.Br[C:6]1[C:7]([NH:11][C@H:12]([C:17]([NH:19][CH2:20][C:21]#[N:22])=[O:18])[CH2:13][CH:14]([CH3:16])[CH3:15])=[N:8][S:9][CH:10]=1.C(OC([N:30]1[CH2:35][CH2:34][N:33]([C:36]2[CH:41]=[CH:40][C:39](B(O)O)=[CH:38][CH:37]=2)[CH2:32][CH2:31]1)=O)(C)(C)C>>[C:21]([CH2:20][NH:19][C:17](=[O:18])[C@H:12]([CH2:13][CH:14]([CH3:16])[CH3:15])[NH:11][C:7]1[C:6]([C:39]2[CH:38]=[CH:37][C:36]([N:33]3[CH2:32][CH2:31][NH:30][CH2:35][CH2:34]3)=[CH:41][CH:40]=2)=[CH:10][S:9][N:8]=1)#[N:22]

Participants

4

Reactant 3

HCID 10901AminoacetonitrileHCID 52330144-(4-BOC-Piperazino)phenylboronic acidHCID 86594561HCID 86594561, compound2×

Product 1

HCID 86594560HCID 86594560, compound

Procedure

Ester hydrolysis and coupling with aminoacetonitrile as described in example 4 provided N2-(4-bromoisothiazol-3-yl)-N1-(cyanomethyl)-L-leucinamide. N2-(4-bromoisothiazol-3-yl)-N1-(cyanomethyl)-L-leucinamide was then treated with 4-[4-(tert-butoxycarbonyl)-1-piperazinyl]phenylboronic acid (prepared as described in Example 1) as described in Example 1 to afford, after BOC removal with methanesulfonic acid as described in Example 10, N1-(cyanomethyl)-N2-[4-(4-piperazin-1-ylphenyl)isothiazol-3-yl]-L-leucinamide. MS (+ESI): 413.2 [M+1]+.

Workup

  1. customto afford
  2. customafter BOC removal with methanesulfonic acid

Sources & evidence

ORD record
ord-8ff0a33ebe744c7aa2072f586e563741
Source dataset
uspto-grants-2006_03
Patent number
US07012075B2

Reaction notes

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