Cyclopropanemethanamine → HCID 67095885, compound

HRID 2076307Notes

Reaction equation

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

Participants

Reactant 2

HCID 75646Cyclopropanemethanamine

HCID 25018803HCID 25018803, compound

Product 1

HCID 67095885HCID 67095885, compound

Conditions

Temperature: 120 °C

Procedure

4-Fluoro-N-[2-((R)-indan-1-ylamino)-quinolin-5-yl]-benzenesulfonamide (product example 1, 0.175 g, 0.404 mmol) was suspended in 2 mL cyclopropanemethylamine. The reaction mixture was stirred in a sealed tube at 120° C. overnight. The reaction mixture was purified by flash chromatography on silica gel (heptan/ethyl acetate 100:0->50:50 gradient). The title compound was obtained as a white solid (46 mg, 24%), MS: m/e=485.5 (M+H+).

Workup

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

Sources & evidence

ORD record: ord-906b19b81575495591b770664fe25687
Source dataset: uspto-grants-2011_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07923561B2

Reaction notes

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