Cesium carbonate → HCID 178511041, compound

HRID 1641316Notes

Reaction equation

HRID 1641316 reaction equation
[NH2:1][C:2]1[CH:33]=[CH:32][CH:31]=[CH:30][C:3]=1[CH2:4][N:5]1[CH2:29][CH2:28][C:8]2([N:12]([C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([F:19])[CH:14]=3)[C:11](=[O:20])[N:10]=[C:9]2[NH:21][CH:22]2[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]2)[CH2:7][CH2:6]1.Br[CH2:35][CH2:36][CH2:37][C:38]#[N:39].C([O-])([O-])=O.[Cs+].[Cs+]>CC#N>[CH:22]1([NH:21][C:9]2[C:8]3([CH2:28][CH2:29][N:5]([CH2:4][C:3]4[CH:30]=[CH:31][CH:32]=[CH:33][C:2]=4[NH:1][CH2:35][CH2:36][CH2:37][C:38]#[N:39])[CH2:6][CH2:7]3)[N:12]([C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([F:19])[CH:14]=3)[C:11](=[O:20])[N:10]=2)[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27]1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 214124-BromobutyronitrileHCID 178507494HCID 178507494, compound

Product 1

HCID 178511041HCID 178511041, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

A 2 mL CH3CN suspension of 0.05 g (0.11 mmol) 8-(2-aminobenzyl)-4-(cyclohexylamino)-1-(3-fluorophenyl)-1,3,8-triazaspiro[4.5]dec-3-en-2-one (example 80), excess 4-bromobutyronitrile and Cs2CO3 was heated to 60° C. and allowed to stir for 2 days. HPLC/MS showed a small amount of product so the reaction was filtered and concentrated. The remaining oil was purified on an Isco automated system affixed with a Biotage Flash 25(M) cartridge eluted with 0-5% MeOH+0.5M NH3 in CH2Cl2 over 30 min at 20 mL/min. The product eluted last.

Workup

  1. filtrationwas filtered
  2. concentrationconcentrated
  3. customThe remaining oil was purified on an Isco automated system
  4. washeluted with 0-5% MeOH+0.5M NH3 in CH2Cl2 over 30 min at 20 mL/min
  5. washThe product eluted last

Sources & evidence

ORD record
ord-74aedacff2444845a379ad0cec80793f
Source dataset
uspto-grants-2012_02
Patent number
US08114887B2

Reaction notes

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