Acetyl chloride → HCID 178474151, compound

HRID 1641314Notes

Reaction equation

HRID 1641314 reaction equation
[CH:1]1([NH:7][C:8]2[C:12]3([CH2:17][CH2:16][N:15]([CH2:18][C:19]4[CH:24]=[CH:23][CH:22]=[C:21]([NH2:25])[CH:20]=4)[CH2:14][CH2:13]3)[N:11]([C:26]3[CH:31]=[CH:30][CH:29]=[C:28]([F:32])[CH:27]=3)[C:10](=[O:33])[N:9]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:34](Cl)(=[O:36])[CH3:35].C([O-])([O-])=O.[K+].[K+]>C(Cl)Cl>[CH:1]1([NH:7][C:8]2[C:12]3([CH2:17][CH2:16][N:15]([CH2:18][C:19]4[CH:20]=[C:21]([NH:25][C:34](=[O:36])[CH3:35])[CH:22]=[CH:23][CH:24]=4)[CH2:14][CH2:13]3)[N:11]([C:26]3[CH:31]=[CH:30][CH:29]=[C:28]([F:32])[CH:27]=3)[C:10](=[O:33])[N:9]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 11430Potassium CarbonateHCID 178507564HCID 178507564, compound

Product 1

HCID 178474151HCID 178474151, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A 2 mL CH2Cl2 suspension of 0.05 g (0.11 mmol) 4-(cyclohexylamino)-8-[3-aminobenzyl]-1-(3-fluorophenyl)-1,3,8-triazaspiro[4.5]dec-3-en-2-one, 0.1 mL (0.11 mmol) acetyl chloride and excess K2CO3 was allowed to stir at rt overnight. The reaction was filtered and concentrated then the remaining oil was dissolved in 1 mL CH2Cl2 and purified on an Isco automated system affixed with a Biotage Flash 25(S) cartridge eluted at 20 mL/min with 0-5% MeOH in CH2Cl2 over 15 min and hold at 5% MeOH for 30 min. The product eluted second, pure by HPLC/MS and NMR.

Workup

  1. filtrationThe reaction was filtered
  2. concentrationconcentrated
  3. dissolutionthe remaining oil was dissolved in 1 mL CH2Cl2
  4. custompurified on an Isco automated system
  5. washeluted at 20 mL/min with 0-5% MeOH in CH2Cl2 over 15 min
  6. waithold at 5% MeOH for 30 min
  7. washThe product eluted second, pure by HPLC/MS and NMR

Sources & evidence

ORD record
ord-7fd354e5c54a4a759a8f9db8e2c26f1b
Source dataset
uspto-grants-2012_02
Patent number
US08114887B2

Reaction notes

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