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4-Pyridinemethanamine → 3-fluoro-5-iodo-N,N-dimethyl-2-[(pyridin-4-ylmethyl)-amino]-benzamide

HRID 2234684
Notes
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Reaction equation

HRID 2234684 reaction equation
F[C:2]1[C:12]([F:13])=[CH:11][C:10]([I:14])=[CH:9][C:3]=1[C:4]([N:6]([CH3:8])[CH3:7])=[O:5].[NH2:15][CH2:16][C:17]1[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=1.C(N(C(C)C)CC)(C)C>O1CCOCC1>[F:13][C:12]1[C:2]([NH:15][CH2:16][C:17]2[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=2)=[C:3]([CH:9]=[C:10]([I:14])[CH:11]=1)[C:4]([N:6]([CH3:8])[CH3:7])=[O:5]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 773174-PyridinemethanamineHCID 81531DiisopropylethylamineHCID 579757722,3-difluoro-5-iodo-N,N-dimethyl-benzamide

Product 1

HCID 577315523-fluoro-5-iodo-N,N-dimethyl-2-[(pyridin-4-ylmethyl)-amino]-benzamideYield 99.9%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
75 °C

Procedure

2,3-Difluoro-5-iodo-N,N-dimethyl-benzamide (507, 1.63 mmol), 4-(aminomethyl)-pyridine (1.8 ml, 17.73 mmol), di-iso-propylethylamine (0.31 ml, 1.78 mmol), and dioxane (3 ml) were combined and stirred for 18 hours at 75° C. The reaction mixture was concentrated in vacuo to give approximately 650 mg of crude 3-fluoro-5-iodo-N,N-dimethyl-2-[(pyridin-4-ylmethyl)-amino]-benzamide, which was used directly in the next step. MS: m/z 400.2 (M+H+).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-50c58df3dbba4c6f8abbd4b07732962e
Source dataset
uspto-grants-2010_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07709645B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes