(6-Bromo-4-chloro-7-fluoroquinolin-3-yl)(cyclopropyl)methanone → HCID 178454021, compound

HRID 2271598Notes

Reaction equation

HRID 2271598 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[F:12])[N:8]=[CH:7][C:6]([C:13]([CH:15]1[CH2:17][CH2:16]1)=[O:14])=[C:5]2Cl.[NH2:19][C@H:20]1[CH2:25][CH2:24][C@H:23]([NH:26][C:27](=[O:33])[O:28][C:29]([CH3:32])([CH3:31])[CH3:30])[CH2:22][CH2:21]1>>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[F:12])[N:8]=[CH:7][C:6]([C:13]([CH:15]1[CH2:17][CH2:16]1)=[O:14])=[C:5]2[NH:19][C@H:20]1[CH2:25][CH2:24][C@H:23]([NH:26][C:27](=[O:33])[O:28][C:29]([CH3:31])([CH3:30])[CH3:32])[CH2:22][CH2:21]1

Participants

3

Reactant 2

HCID 66715407(6-Bromo-4-chloro-7-fluoroquinolin-3-yl)(cyclopropyl)methanoneHCID 178419079HCID 178419079, compound

Product 1

HCID 178454021HCID 178454021, compoundYield 75%

Procedure

Following general procedure B, (6-bromo-4-chloro-7-fluoroquinolin-3-yl)(cyclopropyl)methanone (350 mg, 1.06 mmol) was reacted with tert-butyl trans-4-aminocyclohexylcarbamate (270 mg, 1.27 mmol) to afford the desired product (400 mg, 75%) as a light yellow solid: 1H NMR (300 MHz, CDCl3) δ 10.67 (d, J=8.3 Hz, 1H), 9.22 (s, 1H), 8.32 (d, J=7.3 Hz, 1H), 7.62 (d, J=9.5 Hz, 1H), 4.42 (s, 1H), 3.91 (d, J=8.1 Hz, 1H), 3.52 (s, 1H), 2.75-2.56 (m, 1H), 2.18 (t, J=13.4 Hz, 4H), 1.72-1.62 (m, 1H), 1.59-1.50 (m, 2H), 1.45 (s, 9H), 1.30-1.18 (m, 3H), 1.13-1.01 (m, 2H).

Sources & evidence

ORD record
ord-f5493e9b705746288dfdb2a1bdf6e607
Source dataset
uspto-grants-2015_09
Patent number
US09120749B2

Reaction notes

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