Trifluoroacetic acid → HCID 59834617, compound

HRID 271618Notes

Reaction equation

HRID 271618 reaction equation
[C:1]([C:3]1[N:4]=[CH:5][C:6]2[CH:11]=[C:10]([CH2:12][N:13]3[C:17](=[O:18])[C:16]4([CH2:23][CH2:22][N:21](C(O)=O)[CH2:20][CH2:19]4)[N:15]([CH3:27])[C:14]3=[O:28])[N:9]([CH2:29][C:30]([CH3:33])([CH3:32])[CH3:31])[C:7]=2[N:8]=1)#[N:2].C(O)(C(F)(F)F)=O.C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH3:31][C:30]([CH3:33])([CH3:32])[CH2:29][N:9]1[C:7]2[N:8]=[C:3]([C:1]#[N:2])[N:4]=[CH:5][C:6]=2[CH:11]=[C:10]1[CH2:12][N:13]1[C:17](=[O:18])[C:16]2([CH2:19][CH2:20][NH:21][CH2:22][CH2:23]2)[N:15]([CH3:27])[C:14]1=[O:28]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 86597000HCID 86597000, compound

Product 1

HCID 59834617HCID 59834617, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 7.62 g (0.015 moles) of 3-[2-cyano-7-(2,2-dimethyl-propyl)-7H-pyrrolo[2,3-d]pyrimidin-6-ylmethyl]-1-methyl-2,4-dioxo-1,3,8-triaza-spiro[4.5]decane-8-carboxylic acid .tert.-butyl ester in 30 ml of CH2Cl2, 30 ml (389 mmoles) of TFA is added at 0° C. After bing stirred for 1 hour at ambient temperature, sat. NaHCO3 is added at 0° C. to the reaction mixture and the mixture is extracted with CH2Cl2. The combined extracts are dried over MgSO4 and concentrated under reduced pressure to give desired 7-(2,2-dimethyl-propyl)-6-(1-methyl-2,4-dioxo-1,3,8-triaza-spiro[4.5]dec-3-ylmethyl)-7H-pyrrolo[2,3-d]pyrimidine-2-carbonitrile in quantitative yield. The crude product is used for the next step without purification.

Workup

  1. extractionthe mixture is extracted with CH2Cl2
  2. dry with materialThe combined extracts are dried over MgSO4
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-21229ad3f5f5477e86fbd7ff5e47e6e7
Source dataset
uspto-grants-2008_11
Patent number
US07452886B2

Reaction notes

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