Acetic Acid → HCID 69922784, compound

HRID 2119975Notes

Reaction equation

[CH3:1][C:2]1[C:6]2=[CH:7][C:8]3[CH:22]=[N:21][CH:20]=[N:19][C:9]=3[C:10]3[CH:15]=[CH:14][CH:13]=[C:12]([C:16]([OH:18])=O)[C:11]=3[N:5]2[CH2:4][N:3]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.O[NH:36][C:37]([CH:39]1[CH2:41][CH2:40]1)=[NH:38].C(O)(=O)C>CN(C=O)C>[CH:39]1([C:37]2[N:38]=[C:16]([C:12]3[C:11]4[N:5]5[CH2:4][N:3]=[C:2]([CH3:1])[C:6]5=[CH:7][C:8]5[CH:22]=[N:21][CH:20]=[N:19][C:9]=5[C:10]=4[CH:15]=[CH:14][CH:13]=3)[O:18][N:36]=2)[CH2:41][CH2:40]1

Participants

Conditions

Temperature: 85 °C

Procedure

To a suspension of 6-methyl-9H-imidazo[1,5-a]pyrimido[5,4-d][1]benzazepine-10-carboxylic acid (1.0 g, 3.4 mmol) in DMF (15 mL) was added 1,1′-carbonyldiimidazole (0.61 g, 3.76 mmol) followed by N-hydroxy-cyclopropanecarboxamidine and the resulting solution was heated at 85° C. for 1.5 h. Then acetic acid (3.4 mL) was added and the resulting mixture heated at 130° C. for 40 min. After cooling, the mixture was evaporated and dissolved n DCM (15 mL). This DCM extract was washed with sodium hydrogen carbonate (saturated solution, 40 mL) and then the aqueous phase was washed with DCM (20 mL). The combined DCM layers were then dried over MgSO4 and evaporated. The residue was recrystallized from ethyl acetate: hexane to afford the product (720 mg, 59%) as white crystals, mp 216-218° C., m/z 356 (M).

Workup

temperaturethe resulting mixture heated at 130° C. for 40 min
temperatureAfter cooling
customthe mixture was evaporated
dissolutiondissolved n DCM (15 mL)
extractionThis DCM extract
washwas washed with sodium hydrogen carbonate (saturated solution, 40 mL)
washthe aqueous phase was washed with DCM (20 mL)
dry with materialThe combined DCM layers were then dried over MgSO4
customevaporated
customThe residue was recrystallized from ethyl acetate

Sources & evidence

ORD record: ord-b784e92cd7f14ec1a3c8eb947bf61ef6
Source dataset: uspto-grants-2004_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06686352B2

Reaction notes

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