(R)-(-)-1-Aminoindan → HCID 25018803, compound

HRID 2076277Notes

Reaction equation

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

Participants

Reactant 2

HCID 2733933(R)-(-)-1-Aminoindan

HCID 86619495HCID 86619495, compound

Product 1

HCID 25018803HCID 25018803, compound

Procedure

N-(2-Chloro-quinolin-5-yl)-4-fluoro-benzenesulfonamide (300 mg, 0.891 mmol) and (R)-1-aminoindane (254 mg, 1.91 mmol) were stirred in a sealed tube at 120° C. overnight. The reaction mixture was purified by flash chromatography on silica gel (cyclohexane/ethyl acetate 100:0->50:50 gradient). The title compound was obtained as a yellow solid (287 mg, 74%), MS:

Workup

customThe reaction mixture was purified by flash chromatography on silica gel (cyclohexane/ethyl acetate 100:0->50:50 gradient)

Sources & evidence

ORD record: ord-b63f11b3869346738c214edab5a0d786
Source dataset: uspto-grants-2011_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07923561B2

Reaction notes

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