HCID 59852749, compound → HCID 11292513, compound

HRID 2373919Notes

Reaction equation

[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([C:17]2[N:18]=[C:19]([CH:27]3[CH2:30][CH2:29][CH2:28]3)[N:20]3[CH:25]=[CH:24][N:23]=[C:22](Cl)[C:21]=23)[CH:12]=[CH:13][C:14]=1[O:15][CH3:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(OC1C=C(C(NC(C2CCC2)=O)C2C(Cl)=NC=C[N:49]=2)C=CC=1OC)C1C=CC=CC=1>O=P(Cl)(Cl)Cl>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([C:17]2[N:18]=[C:19]([CH:27]3[CH2:30][CH2:29][CH2:28]3)[N:20]3[CH:25]=[CH:24][N:23]=[C:22]([NH2:49])[C:21]=23)[CH:12]=[CH:13][C:14]=1[O:15][CH3:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 55 °C

Procedure

1-(3-Benzyloxy-4-methoxyphenyl)-8-chloro-3-cyclobutylimidazo[1,5-a]pyrazine: Cyclobutanecarboxylic acid [(3-benzyloxy-4-methoxyphenyl)-(3-chloropyrazin-2-yl)-methyl]-amide (308 mg, 0.703 mmol) was dissolved in POCl3 (5 ml) and heated at 55° C. for 17 h. After that time, the excess POCl3 was removed in vacuo and the remaining mixture was basified with NH3 (2 N in iPrOH). The precipitate formed was filtered off and washed with CH2Cl2, and the filtrate was purified by chromatography on silica gel to obtain a yellow-brown solid of the title compound (87% purity by LC-MS); 1H NMR (DMSO-d6, 400 MHz) δ 2.03-2.20 (m, 2H), 2.47-2.67 (m, 4H), 3.95 (s, 3H), 5.22 (s, 2H), 7.00 (d, 1H, J=8.0 Hz), 7.25-7.47 (m, 8H); MS (ES): 420.0/422.1 (M/M+2).

Workup

customAfter that time, the excess POCl3 was removed in vacuo
customThe precipitate formed
filtrationwas filtered off
washwashed with CH2Cl2
customthe filtrate was purified by chromatography on silica gel

Sources & evidence

ORD record: ord-ee8aa3dc4b934fe1832fb42b1f2edbe1
Source dataset: uspto-grants-2008_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07459554B2

Reaction notes

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