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Triethylamine → N-(3-(4-fluorophenoxy)phenyl)-4-methyl-1-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidine-4-carboxamide

HRID 216025
Notes
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Reaction equation

HRID 216025 reaction equation
[F:1][C:2]1[CH:24]=[CH:23][C:5]([O:6][C:7]2[CH:8]=[C:9]([NH:13][C:14]([C:16]3([CH3:22])[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]3)=[O:15])[CH:10]=[CH:11][CH:12]=2)=[CH:4][CH:3]=1.Cl[C:26]1[C:27]2[CH:34]=[CH:33][NH:32][C:28]=2[N:29]=[CH:30][N:31]=1.C(N(CC)CC)C>C(O)(C)C>[F:1][C:2]1[CH:24]=[CH:23][C:5]([O:6][C:7]2[CH:8]=[C:9]([NH:13][C:14]([C:16]3([CH3:22])[CH2:17][CH2:18][N:19]([C:26]4[C:27]5[CH:34]=[CH:33][NH:32][C:28]=5[N:29]=[CH:30][N:31]=4)[CH2:20][CH2:21]3)=[O:15])[CH:10]=[CH:11][CH:12]=2)=[CH:4][CH:3]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 53566827H-Pyrrolo(2,3-d)pyrimidine, 4-chloro-HCID 67036908N-(3-(4-fluorophenoxy)phenyl)-4-methylpiperidine-4-carboxamide

Product 1

HCID 57920193N-(3-(4-fluorophenoxy)phenyl)-4-methyl-1-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidine-4-carboxamide

Reagents, catalysts & solvents 1

HCID 3776Isopropanol
Solvent

Conditions

Temperature
180 °C

Procedure

To a solution of N-(3-(4-fluorophenoxy)phenyl)-4-methylpiperidine-4-carboxamide from example 1, step B, (20 mg, 0.05 mmol) in isopropanol (1 mL), was added 4-chloro-7H-pyrrolo[2,3-d]pyrimidine (15 mg, 0.1 mmol) and triethylamine (0.04 mL, 0.3 mmol). The reaction mixture was heated at 180° C. for 30 minutes under microwave conditions, and then concentrated under vacuum. The product was isolated by prep HPLC to give the title compound.

Workup

  1. concentrationconcentrated under vacuum
  2. customThe product was isolated by prep HPLC

Sources & evidence

ORD record
ord-57c6a778a7f34ea6af5b7666e4aafcf8
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