Cyclopropylamine → HCID 11504648, compound

HRID 1927465Notes

Reaction equation

[CH:1]1([NH2:4])[CH2:3][CH2:2]1.[CH3:5][O:6][C:7]([C:9]1[CH:10]=[C:11]([CH3:35])[C:12]2[O:18][C:17]3[C:19]([Cl:31])=[CH:20][C:21]([N:23]([C:27](=[O:30])[CH2:28]Cl)[CH2:24][CH2:25]Cl)=[CH:22][C:16]=3[CH2:15][S:14](=[O:33])(=[O:32])[C:13]=2[CH:34]=1)=[O:8]>CN(C=O)C>[CH3:5][O:6][C:7]([C:9]1[CH:10]=[C:11]([CH3:35])[C:12]2[O:18][C:17]3[C:19]([Cl:31])=[CH:20][C:21]([N:23]4[CH2:24][CH2:25][N:4]([CH:1]5[CH2:3][CH2:2]5)[CH2:28][C:27]4=[O:30])=[CH:22][C:16]=3[CH2:15][S:14](=[O:32])(=[O:33])[C:13]=2[CH:34]=1)=[O:8]

Participants

Conditions

Temperature: 50 °C

Procedure

Cyclopropylamine (0.082 mL, 1.18 mmol) was added to a solution of Example 57k (0.2 g, 0.39 mmol) in DMF (5 mL) and stirred at 50° C. for 1.5 h. The reaction mixture was concentrated to obtain the title compound which was purified using flash chromatography (silica gel, 1.5% methanol/chloroform). Yield: 0.135 g (71%); 1H NMR (CDCl3): δ 0.49 (m, 2H, CH2), 0.56 (m, 2H, CH2), 1.77 (m, 1H, CH), 2.70 (s, 3H, CH3), 3.01 (t, 2H, CH2), 3.82 (s, 2H, CH2), 3.67 (t, 2H, CH2), 3.92 (s, 3H, OCH3), 4.70 (s, 2H, CH2), 7.36 (s, 1H, Ar), 7.44 (d, 1H, Ar), 8.10 (s, 1H, Ar), 8.46 (d, 1H, Ar); MS: m/e (ES+) 491 (M+1).

Workup

concentrationThe reaction mixture was concentrated

Sources & evidence

ORD record: ord-096594deb9e940078991afe0d37ef07e
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08183234B2

Reaction notes

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