3,5-Difluorobenzoic acid → HCID 10173638, compound

HRID 2415623Notes

Reaction equation

HRID 2415623 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([NH:12][C@H:13]3[CH2:18][C@@H:17]([CH3:19])[C@@H:16]([NH2:20])[CH2:15][C@H:14]3[CH3:21])=[CH:7][CH:8]=[N:9]2)=[CH:4][CH:3]=1.ClC1C=C2C(C(NC3CCC(N)CC3)=CC=N2)=CC=1.[F:41][C:42]1[CH:43]=[C:44]([CH:48]=[C:49]([F:51])[CH:50]=1)[C:45](O)=[O:46].N1C2C(=CC=C(C(O)=O)C=2)C=C1>>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([NH:12][C@@H:13]3[C@H:14]([CH3:21])[CH2:15][C@H:16]([NH:20][C:45](=[O:46])[C:44]4[CH:43]=[C:42]([F:41])[CH:50]=[C:49]([F:51])[CH:48]=4)[C@H:17]([CH3:19])[CH2:18]3)=[CH:7][CH:8]=[N:9]2)=[CH:4][CH:3]=1

Participants

5

Reactant 4

HCID 1012653,5-Difluorobenzoic acidHCID 5952301H-indole-6-carboxylic acidHCID 18391686N-(7-chloroquinolin-4-yl)cyclohexane-1,4-diamineHCID 69921757HCID 69921757, compound

Product 1

HCID 10173638HCID 10173638, compound

Procedure

The titled compound was prepared according to the method described in Example 23 substituting (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 and 3,5-difluorobenzoic acid for indole-6-carboxylic acid. 1H NMR (300 MHz, DMSO) δ ppm 8.87 (d, 1 H), 8.55 (t, 1 H), 8.07 (d, 1 H), 7.93 (d, 1 H), 7.83 (dd, 1 H), 7.42-7.64 (m, 4 H), 7.00 (d, 1 H), 4.00-4.20 (m, 2 H), 1.63-2.34 (m, 6 H), 1.03 (d, 3 H), 1.00 (d, 3 H). MS(ESI(+)Q1MS m/z 444 (M+H)+).

Sources & evidence

ORD record
ord-460fedc06b154afdb14fd93fdbccdc65
Source dataset
uspto-grants-2004_11
Patent number
US06818772B2

Reaction notes

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