Ammonium Chloride → HCID 59834677, compound

HRID 271616Notes

Reaction equation

HRID 271616 reaction equation
C([N:8]1[CH2:36][CH2:35][C:11]2([O:15][C:14](=[O:16])[N:13]([CH2:17][C:18]3[N:28]([CH2:29][C:30]([CH3:33])([CH3:32])[CH3:31])[C:21]4[N:22]=[C:23]([C:26]#[N:27])[N:24]=[CH:25][C:20]=4[CH:19]=3)[C:12]2=[O:34])[CH2:10][CH2:9]1)C1C=CC=CC=1.Cl[C:38]([O:40][CH2:41][C:42]([Cl:45])([Cl:44])[Cl:43])=[O:39].[NH4+].[Cl-]>CC#N>[Cl:43][C:42]([Cl:45])([Cl:44])[CH2:41][O:40][C:38]([N:8]1[CH2:36][CH2:35][C:11]2([O:15][C:14](=[O:16])[N:13]([CH2:17][C:18]3[N:28]([CH2:29][C:30]([CH3:32])([CH3:33])[CH3:31])[C:21]4[N:22]=[C:23]([C:26]#[N:27])[N:24]=[CH:25][C:20]=4[CH:19]=3)[C:12]2=[O:34])[CH2:10][CH2:9]1)=[O:39]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 870632,2,2-Trichloroethyl chloroformateHCID 59834590HCID 59834590, compound

Product 1

HCID 59834677HCID 59834677, compoundYield 97.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 0.22 g (0.45 mmoles) of 6-(8-benzyl-2,4-dioxo-1-oxa-3,8-diaza-spiro[4.5]dec-3-ylmethyl)-7-(2,2-dimethyl-propyl)-7H-pyrrolo[2,3-d]pyrimidine-2-carbonitrile in 4 ml of CH3CN is added 2,2,2-trichloroethyl chloroformate(0.91 mmol) at ambient temperature and the mixture is stirred for 18 hours. Aqueous NH4Cl is added and the organic layer is extracted with AcOEt, washed with brine, dried over Na2SO4 and concentrated. The crude product is purified by silica gel column chromatography (n-Hexane:AcOEt=1:1) to give 0.25 g of 3-[2-cyano-7-(2,2-dimethyl-propyl)-7H-pyrrolo[2,3-d]pyrimidin-6-ylmethyl]-2,4-dioxo-1-oxa-3,8-diaza-spiro[4.5]decane-8-carboxylic acid 2,2,2-trichloro-ethyl ester in 96% yield.

Workup

  1. extractionthe organic layer is extracted with AcOEt
  2. washwashed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customThe crude product is purified by silica gel column chromatography (n-Hexane:AcOEt=1:1)

Sources & evidence

ORD record
ord-91f078d6901044c99c1da4733c3b4cd7
Source dataset
uspto-grants-2008_11
Patent number
US07452886B2

Reaction notes

Loading…