Formamidine acetate → HCID 57758181, compound

HRID 2197524Notes

Reaction equation

C(O)(=O)C.[CH:5](N)=[NH:6].[NH2:8][N:9]1[C:13]([C:14]#[N:15])=[C:12]([C:16]2[CH:21]=[CH:20][C:19]([NH2:22])=[C:18]([F:23])[CH:17]=2)[C:11]([C:24]([O:26][CH2:27][CH3:28])=[O:25])=[CH:10]1>C(O)CCC>[NH2:15][C:14]1[C:13]2=[C:12]([C:16]3[CH:21]=[CH:20][C:19]([NH2:22])=[C:18]([F:23])[CH:17]=3)[C:11]([C:24]([O:26][CH2:27][CH3:28])=[O:25])=[CH:10][N:9]2[N:8]=[CH:5][N:6]=1

Participants

Conditions

Temperature: 100 °C

Procedure

Formamidine acetate (22.4 g, 215 mmol) was added to a suspension of ethyl 1-amino-4-(4-amino-3-fluorophenyl)-5-cyano-1H-pyrrole-3-carboxylate (6.2 g, 21.5 mmol) in n-butanol (100 mL). The reaction was heated (100° C.) for 16 h and then cooled to rt. The solvent was removed under reduced pressure and then ethanol (50 mL) and water (200 mL) were added. The mixture was stirred for 30 min and the resulting precipitate was collected by filtration. The solid was washed with water (2×50 mL) and dried to afford desired product (5.80 g, 85%); 1H NMR (300 MHz, DMSO-d6) δ 8.08 (s, 1H), 8.00-8.10 (br s, 1H), 7.90 (s, 1H), 7.03 (dd, J=12.3, 1.9 Hz, 1H), 6.77-6.88 (m, 2H), 5.36 (s, 2H), 5.21-5.31 (br s, 1H), 4.06 (q, J=7.1 Hz, 2H), 1.11 (t, J=7.1 Hz, 3H); ES-MS m/z 316.4 (MH)+; HPLC RT (Method B) 2.39 min.

Workup

temperaturecooled to rt
customThe solvent was removed under reduced pressure
additionethanol (50 mL) and water (200 mL) were added
filtrationthe resulting precipitate was collected by filtration
washThe solid was washed with water (2×50 mL)
customdried

Sources & evidence

ORD record: ord-5f6fb708a09b4f8888c184a1931bb29e
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08338594B2

Reaction notes

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