tert-butyl N-{3-[(3-aminopropyl)(methyl)amino]propyl}carbamate → HCID 178483846, compound

HRID 12260Notes

Reaction equation

Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]([CH3:12])[C:4]2=[C:13]3[C:18](=[N:19][C:3]=12)[CH:17]=[CH:16][CH:15]=[CH:14]3.[C:20]([O:24][C:25](=[O:36])[NH:26][CH2:27][CH2:28][CH2:29][N:30]([CH2:32][CH2:33][CH2:34][NH2:35])[CH3:31])([CH3:23])([CH3:22])[CH3:21]>C(OCCO)C>[C:20]([O:24][C:25](=[O:36])[NH:26][CH2:27][CH2:28][CH2:29][N:30]([CH3:31])[CH2:32][CH2:33][CH2:34][NH:35][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]([CH3:12])[C:4]2=[C:13]3[C:18](=[N:19][C:3]=12)[CH:17]=[CH:16][CH:15]=[CH:14]3)([CH3:23])([CH3:22])[CH3:21]

Participants

Conditions

Temperature: 120 °C

Procedure

A solution of 11-chloro-5-methyl-5H-indolo[3,2-b]quinoline (cf. Bierer et al., J. Med. Chem. 1998, vol. 41, pp. 2754) (61 mg, 0.23 mmol) and [[3-[(3-amino-propyl)methylamino]propyl]carbamic acid tert-butyl ester previously prepared (Spicer at el., Bioorg. Med. Chem. 2002, vol. 10, p. 19) (84_l, 0.34 mmol) in 2-ethoxyethanol (10 ml) was heated at 120° C. for 10 min. Removal of the solvent and purification by chromatography on alumina (CHCl3: MeOH 2%) yielded [3-[methyl-[3-(5-methyl-5H-indolo[3,2-b]quinolin-11-yl-amino)propyl]-amino]propyl]carbamic acid tert-butyl ester (49 mg, 490%) as a foam. 1H NMR [CDCl3—, ppm]: 8.16 (d, J=8.5 Hz, 1H), 7.81 (m, 4H), 7.55-7.48 (m, 2H), 7.21 (m, 1H), 4.51 (s, 3H, NCH3), 4.27 (m, 2H, CH2NO), 3.12 (m, 2H, CH2NHBOC), 2.76 (m, 2H, CH2N(CH3)), 2.63 (m, 2H, CH2N(CH3)), 2.39 (s, 3H, N(CH3)), 2.34 (m, 2H, CH2CN(CH3)), 1.73 (m, 2H, CH2CN(CH3)), 1.37 (s, 9H, C(CH3)3).

Workup

customRemoval of the solvent and purification by chromatography on alumina (CHCl3: MeOH 2%)

Sources & evidence

ORD record: ord-2f3f5155806b4c4baa1dd17e76b333bc
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07728000B2

Reaction notes

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