3-Iodobenzoic acid → 3-iodo-N-(1-(pyridin-2-yl)cyclopropyl)benzamide

HRID 2068414

Reaction equation

HRID 2068414 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=O.[N:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[C:17]1([NH2:20])[CH2:19][CH2:18]1.CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C>C(Cl)Cl.O>[I:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([NH:20][C:17]1([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][N:11]=2)[CH2:19][CH2:18]1)=[O:7]

Participants

8

Reactant 5

HCID 120603-Iodobenzoic acidHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 111054091-(Pyridin-2-yl)cyclopropanamine

Product 1

HCID 672176523-iodo-N-(1-(pyridin-2-yl)cyclopropyl)benzamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

3-Iodobenzoic acid (2.7 g, 11.1 mmol, 1 eq), 1-(pyridin-2-yl)cyclopropanamine (1.5 g, 11.1 mmol, 1 eq), EDCI.HCl (3.2 g, 16.7 mmol, 1.5 eq), HOBT (2.2 g, 16.7 mmol, 1.5 eq) and DIPEA (6 ml, 33.5 mmol, 3 eq) were dissolved in DCM and the resulting mixture was stirred at room temperature for 18 hours. Water was added to the mixture and the product was extracted with DCM. The organic layer was concentrated and the product crystallized using dichloromethane and hexane. Yield: 2.3 g (57%). 1HNMR (400 MHz, DMSO-d6): δ 1.26 (m, 2H), 1.54 (m, 2H), 7.13 (t, J=4.04 Hz, 1H), 7.29 (m, 2H), 7.69 (t, J=8.06 Hz, 1H), 7.92 (d, J=3.05 Hz, 2H), 8.29 (s, 1H), 8.45 (d, J=4.56 Hz, 1H), 9.33 (s, 1H).

Workup

  1. extractionthe product was extracted with DCM
  2. concentrationThe organic layer was concentrated
  3. customthe product crystallized

Sources & evidence

ORD record
ord-39e2177816c843dab1eaae166f78e304
Source dataset
uspto-grants-2012_10
Patent number
US08293909B2

Linked notes

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