Isatoic Anhydride → N-cyclopropyl-2-[(4,5-dihydro-1H-imidazol-2-ylmethyl)amino]benzamide

HRID 1816253Notes

Reaction equation

[NH2:1][C:2]1[CH:13]=[CH:12][CH:11]=[CH:10][C:3]=1[C:4]([NH:6][CH:7]1[CH2:9][CH2:8]1)=[O:5].[CH:14]1([NH2:17])[CH2:16]C1.[C:18]12[C:24](=CC=CC=1)[NH:23]C(=O)OC2=O>>[CH:7]1([NH:6][C:4](=[O:5])[C:3]2[CH:10]=[CH:11][CH:12]=[CH:13][C:2]=2[NH:1][CH2:16][C:14]2[NH:17][CH2:18][CH2:24][N:23]=2)[CH2:8][CH2:9]1

Participants

Reactant 3

HCID 8359Isatoic Anhydride

HCID 69828Cyclopropylamine

HCID 20600072-amino-N-cyclopropylbenzamide

Product 1

HCID 10199052N-cyclopropyl-2-[(4,5-dihydro-1H-imidazol-2-ylmethyl)amino]benzamide

Procedure

2-Amino-N-cyclopropylbenzamide (prepared from cyclopropylamine and isatoic anhydride, using the methods described in Example 17) and CMI were reacted using conditions described in the general procedure for CMI coupling to give N-cyclopropyl-2-[(4,5-dihydro-1H-imidazol-2-ylmethyl)amino]benzamide, isolated as the hydrochloride salt.

Workup

customwere reacted

Sources & evidence

ORD record: ord-bc8c59d745de41f6a78e0baf64a1a95f
Source dataset: uspto-grants-2005_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06884801B1

Reaction notes

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