Diisopropylethylamine → HCID 44482113, compound

HRID 216056Notes

Reaction equation

HRID 216056 reaction equation
[CH3:1][N:2]([CH3:30])[C:3](=[O:29])[O:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([NH:11][C:12]([C:14]2([CH2:20][O:21][CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]2)=[O:13])[CH:6]=1.C(N(CC)C(C)C)(C)C.Cl[C:41]1[C:42]2[C:49]([CH3:50])=[CH:48][NH:47][C:43]=2[N:44]=[CH:45][N:46]=1>C(O)(C)C.CCOC(C)=O>[CH3:1][N:2]([CH3:30])[C:3](=[O:29])[O:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([NH:11][C:12]([C:14]2([CH2:20][O:21][CH2:22][C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=3)[CH2:15][CH2:16][N:17]([C:41]3[C:42]4[C:49]([CH3:50])=[CH:48][NH:47][C:43]=4[N:44]=[CH:45][N:46]=3)[CH2:18][CH2:19]2)=[O:13])[CH:6]=1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 148092824-Chloro-5-methyl-7H-pyrrolo(2,3-d)pyrimidineHCID 67036889HCID 67036889, compound

Product 1

HCID 44482113HCID 44482113, compoundYield 38%

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
85 °C

Procedure

To a solution of 3-(4-(benzyloxymethyl)piperidine-4-carboxamido)phenyl dimethylcarbamate from step D (0.2 g, 0.49 mmol) in isopropanol (5 mL) was added N,N-diisopropylethylamine (0.167 mL, 0.98 mmol) and 4-chloro-5-methyl-7H-pyrrolo[2,3-d]pyrimidine (0.08 g, 0.49 mmol). The reaction was heated at 85° C. overnight, diluted with EtOAc, washed with brine, dried over MgSO4, and concentrated under vacuum. The residue was purified by flash chromatography (40 g SiO2, 0-80% ethylacetate:hexanes) to give the title compound (0.1 g, 38%).

Workup

  1. washwashed with brine
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated under vacuum
  4. customThe residue was purified by flash chromatography (40 g SiO2, 0-80% ethylacetate:hexanes)

Sources & evidence

ORD record
ord-03fe8678d54d441c80007e40bc351886
Source dataset
uspto-grants-2012_06
Patent number
US08193202B2

Reaction notes

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