Dimethylformamide → 2-amino-N-cyclopropyl-3-iodo-benzamide

HRID 876215Notes

Reaction equation

HRID 876215 reaction equation
[NH2:1][C:2]1[C:10]([I:11])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.CN(C=O)C.CC[N:19]([CH:23]([CH3:25])[CH3:24])C(C)C.C1(N)CC1>O>[NH2:1][C:2]1[C:10]([I:11])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([NH:19][CH:23]1[CH2:25][CH2:24]1)=[O:6]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 69828CyclopropylamineHCID 81531DiisopropylethylamineHCID 2820702-Amino-3-iodobenzoic acid

Product 1

HCID 904166632-amino-N-cyclopropyl-3-iodo-benzamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 2-amino-3-iodo-benzoic acid (200 mg, 0.76 mmol) in DMF (1 mL) TBTU (244.15 mg, 0.76 mmol) and DIPEA (245.69 μL, 1.52 mmol) are added and stirred at r.t. for 7 min. Cyclopropylamine (52.69 μL, 0.76 mmol) is added and stirred at r.t. overnight. The reaction mixture is diluted with water and the precipitate is filtered off and dried.

Workup

  1. stirringstirred at r.t. overnight
  2. filtrationthe precipitate is filtered off
  3. customdried

Sources & evidence

ORD record
ord-6fab1af941164b65aa058acef57b61b5
Source dataset
uspto-grants-2015_03
Patent number
US08987249B2

Reaction notes

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