Butylamine → HCID 10293771, compound

HRID 1797053Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:18]([C:19]3[CH:24]=[CH:23][N:22]=[C:21](F)[CH:20]=3)=[C:11]3[CH:12]=[CH:13][CH:14]=[C:15]([O:16][CH3:17])[N:10]3[N:9]=2)=[CH:4][CH:3]=1.[CH2:26]([NH2:30])[CH2:27][CH2:28][CH3:29]>C(OCC)(=O)C>[CH2:26]([NH:30][C:21]1[CH:20]=[C:19]([C:18]2[C:8]([C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=3)=[N:9][N:10]3[C:15]([O:16][CH3:17])=[CH:14][CH:13]=[CH:12][C:11]=23)[CH:24]=[CH:23][N:22]=1)[CH2:27][CH2:28][CH3:29]

Participants

Conditions

Temperature: 130 °C

Procedure

In a sealed-tube was combined 2-(4Fluorophenyl)-3-(2-fluoro-4-pyridinyl)-7-methoxypyrazolo[1,5-a]pyridine (from Example 30, 20 mg, 0.06 mmol) and n-butylamine (2.0 mL, 1.5 g, 20 mmol), and the reaction was placed in a pre-heated oil bath at 130° C. The reaction was stirred at 130° C. until consumption of starting material was indicated by TLC analysis (50% ethyl acetate in hexanes). The contents of the sealed-tube was transferred to a flask and concentrated to dryness at 50° C. under high vacuum. The residue was purified by silica gel chromatography to yield the title compound, 2.0 mg (0.005 mmol, 80%). 1H NMR (d6-acetone): δ 8.04(d, 1H, J=5.1 Hz), 7.74(dd, 2H, J=5.7, 9.0 Hz), 7.33–7.38(m, 2H), 7.22(t, 2H, J=9.0 Hz), 6.45–6.54(m, 3H), 4.25(s, 3H), 3.30–3.40(m, 2H), 1.60(quint, 2H, J=7.2 Hz), 1.45(sext, 2H, J=7.2 Hz), 0.9(t, 3H, J=7.2 Hz). MS (ES+ve): 391.1 (100, M+), 376.3 (100).

Workup

customIn a sealed-tube was combined
customThe contents of the sealed-tube was transferred to a flask
concentrationconcentrated to dryness at 50° C. under high vacuum
customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record: ord-0bb90ebf000e4d2d9c3a17dc965d2f68
Source dataset: uspto-grants-2006_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07034030B2

Reaction notes

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