Triethylamine → HCID 67970850, compound

HRID 889542Notes

Reaction equation

Cl.Cl.[NH2:3][CH2:4][C:5]1[CH:6]=[CH:7][C:8]([Cl:19])=[C:9]([CH:18]=1)[C:10]([NH:12][C:13]1[NH:14][CH:15]=[CH:16][N:17]=1)=[O:11].[CH3:20][C:21]1([C:24](O)=[O:25])[CH2:23][CH2:22]1.C(N(CC)CC)C.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1>CN(C=O)C>[Cl:19][C:8]1[CH:7]=[CH:6][C:5]([CH2:4][NH:3][C:24]([C:21]2([CH3:20])[CH2:23][CH2:22]2)=[O:25])=[CH:18][C:9]=1[C:10]([NH:12][C:13]1[NH:14][CH:15]=[CH:16][N:17]=1)=[O:11]

Participants

Conditions

Temperature: 60 °C

Procedure

Dissolve 5-(aminomethyl)-2-chloro-N-(1H-imidazol-2-yl)benzamide dihydrochloride (100 mg, 0.35 mmol, 1.0 equiv) and 1-methylcyclopropanecarboxylic acid (45.3 mg, 0.45 mmol, 1.3 equiv) in DMF (0.697 mL), add triethylamine (82.5 μL, 0.59 mmol, 1.7 equiv) and BOP (231 mg, 0.52 mmol, 1.5 equiv). Stir the mixture at 60° C. overnight, and purify the crude mixture by flash chromatography on silica gel eluting with a 20% to 60% EtOAc/hexanes gradient. Recrystallize the material from EtOAc, filter, and wash with EtOAc to provide the title compound as a white solid (116 mg, 55%). 1H NMR (DMSO-d6, 400 MHz) δ 11.76 (br s, 2H), 8.13 (t, 1H, J=6.0 Hz), 7.43 (d, 1H, J=8.2 Hz), 7.39 (d, 1H, J=1.3 Hz), 7.29 (dd, 1H, J=8.2, 1.3 Hz), 6.74 (br s, 2H), 4.25 (d, 2H, J=6.0 Hz), 1.26 (s, 3H), 0.93 (app q, 2H, J=3.1 Hz), 0.50 (app q, 2H, J=3.2 Hz). MS (m/z) (35Cl/37Cl) 333/335 (M+1).

Workup

custompurify the crude mixture by flash chromatography on silica gel eluting with a 20% to 60% EtOAc/hexanes gradient
customRecrystallize the material from EtOAc
filtrationfilter
washwash with EtOAc

Sources & evidence

ORD record: ord-308ba97a8566461f829fd2f62fd67614
Source dataset: uspto-grants-2012_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08252831B2

Reaction notes

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