(R)-N2-Indan-1-yl-quinoline-2,6-diamine → HCID 44218876, compound

HRID 1928774Notes

Reaction equation

FC(F)(F)S([O-])(=O)=O.C[N+]1[CH:14]=[CH:13][N:12]([S:15]([N:18]2[CH2:23][CH2:22][O:21][CH2:20][CH2:19]2)(=[O:17])=[O:16])C=1.[C@H:24]1([NH:33][C:34]2[CH:43]=[CH:42][C:41]3[C:36](=[CH:37][CH:38]=C(N)C=3)[N:35]=2)[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH2:26][CH2:25]1>C(#N)C>[C@H:24]1([NH:33][C:34]2[CH:43]=[CH:42][C:41]3[C:36](=[CH:37][CH:38]=[C:13]([NH:12][S:15]([N:18]4[CH2:19][CH2:20][O:21][CH2:22][CH2:23]4)(=[O:16])=[O:17])[CH:14]=3)[N:35]=2)[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH2:26][CH2:25]1

Participants

Conditions

Temperature: 80 °C

Procedure

1-Methyl-3-(morpholine-4-sulfonyl)-3H-imidazol-1-ium trifluoromethanesulfonate (0.139 g, 0.36 mmol) and (R)—N2-indan-1-yl-quinoline-2,6-diamine (0.10 g, 0.36 mmol) were dissolved in acetonitrile (2 mL) and stirred for 16 h at 80° C. The solvent was removed and the residue subjected to column chromatography (silica gel, heptane, ethyl acetate 4:1/1:1) to yield morpholine-4-sulfonic acid [2-((R)-indan-1-ylamino)-quinolin-6-yl]-amide (0.07 g, 45%) as a yellow solid; MS: m/e=425.7 (M+H+).

Workup

customThe solvent was removed

Sources & evidence

ORD record: ord-45044b9cab3f4697b6a345e318e14b26
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08183380B2

Reaction notes

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