1-Bromo-3,5-difluorobenzene → HCID 10216263, compound

HRID 2415622Notes

Reaction equation

HRID 2415622 reaction equation
Br[C:2]1C=C(F)C=C(F)C=1.[Cl:10][C:11]1[CH:20]=[C:19]2[C:14]([C:15]([NH:21][C@H:22]3[CH2:27][C@@H:26]([CH3:28])[C@@H:25]([NH2:29])[CH2:24][C@H:23]3[CH3:30])=[CH:16][CH:17]=[N:18]2)=[CH:13][CH:12]=1.Cl[C:32]1[CH:41]=[C:40]2[C:35]([C:36](NC3CCC(N)CC3)=CC=N2)=[CH:34][CH:33]=1>>[Cl:10][C:11]1[CH:20]=[C:19]2[C:14]([C:15]([NH:21][C@H:22]3[CH2:27][C@@H:26]([CH3:28])[C@@H:25]([NH:29][C:33]4[CH:32]=[C:41]([CH3:2])[CH:40]=[C:35]([CH3:36])[CH:34]=4)[CH2:24][C@H:23]3[CH3:30])=[CH:16][CH:17]=[N:18]2)=[CH:13][CH:12]=1

Participants

4

Reactant 3

HCID 1363131-Bromo-3,5-difluorobenzeneHCID 18391686N-(7-chloroquinolin-4-yl)cyclohexane-1,4-diamineHCID 69921757HCID 69921757, compound

Product 1

HCID 10216263HCID 10216263, compound

Procedure

The titled compound was prepared according to the methods described in Example 140, substituting 5-bromo-m-xylene for 1-bromo-3,5-difluorobenzene and (1S,2R,4S,5R)-N-(7-chloroquinolin-4-yl)-2,5-dimethylcyclohexane-1,4-diamine for N-(7-chloroquinolin-4-yl)cyclohexane-1,4-diamine. 1H NMR (300 MHz, DMSO) δ ppm 8.89 (d, 1 H), 8.56 (m, 2 H), 7.92 (d, 1 H), 7.82 (dd, 1 H), 6.99 (d, 1 H), 6.31 (s, 2 H), 6.17 (s, 1 H), 4.10 (br.s, 2 H), 2.14 (s, 6 H), 2.03-2.33 (m, 4 H), 1.69 (m, 2 H), 0.97 (br.d, 6 H). MS(ESI(+)Q1MS m/z 408 (M+H)+).

Sources & evidence

ORD record
ord-4b3f55ddbb334167bef2a97ad2aada76
Source dataset
uspto-grants-2004_11
Patent number
US06818772B2

Reaction notes

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