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Diisopropylethylamine → 3-(4-(methoxymethyl)-1-(5-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidine-4-carboxamido)phenyl dimethylcarbamate

HRID 216062
Notes
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Reaction equation

HRID 216062 reaction equation
[CH3:1][N:2]([CH3:24])[C:3](=[O:23])[O:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([NH:11][C:12]([C:14]2([CH2:20][O:21][CH3:22])[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:35]1[C:36]2[C:43]([CH3:44])=[CH:42][NH:41][C:37]=2[N:38]=[CH:39][N:40]=1>C(O)(C)C>[CH3:24][N:2]([CH3:1])[C:3](=[O:23])[O:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([NH:11][C:12]([C:14]2([CH2:20][O:21][CH3:22])[CH2:15][CH2:16][N:17]([C:35]3[C:36]4[C:43]([CH3:44])=[CH:42][NH:41][C:37]=4[N:38]=[CH:39][N:40]=3)[CH2:18][CH2:19]2)=[O:13])[CH:6]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 148092824-Chloro-5-methyl-7H-pyrrolo(2,3-d)pyrimidineHCID 670369673-(4-(Methoxymethyl)piperidine-4-carboxamido)phenyl dimethylcarbamate

Product 1

HCID 579201943-(4-(methoxymethyl)-1-(5-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidine-4-carboxamido)phenyl dimethylcarbamateYield 42%

Reagents, catalysts & solvents 1

HCID 3776
Isopropanol
Solvent

Conditions

Temperature
110 °C

Procedure

To a solution of 3-(4-(methoxymethyl)piperidine-4-carboxamido)phenyl dimethylcarbamate, from step D, and N,N-diisopropylethylamine (2 mL, 11.9 mmol) in isopropanol (5 mL) was added 4-chloro-5-methyl-7H-pyrrolo[2,3-d]pyrimidine (397 mg, 2.37 mmol). The reaction mixture was heated to 110° C. in a sealed high-pressure vial for 17 hours, during which time the mixture became homogenous. The reaction was concentrated under vacuum and purified by silica gel chromatography (3-5% methanol:CH2Cl2). The product was washed with cold methanol to provide the title compound as an off-white solid (462 mg, 42% yield).

Workup

  1. concentrationThe reaction was concentrated under vacuum
  2. custompurified by silica gel chromatography (3-5% methanol:CH2Cl2)
  3. washThe product was washed with cold methanol

Sources & evidence

ORD record
ord-a90a55b966c84de2b59f8f3638fb7632
Source dataset
uspto-grants-2012_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08193202B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes