4-Methylcyclohexylamine → HCID 58692228, compound

HRID 2264248Notes

Reaction equation

[CH3:1][CH:2]1[CH2:7][CH2:6][CH:5]([NH2:8])[CH2:4][CH2:3]1.C1(S([N:18]2[C:22]3=[N:23][CH:24]=[CH:25][CH:26]=[C:21]3[C:20]([C:27]3[CH:32]=[CH:31][N:30]=[C:29](Cl)[N:28]=3)=[CH:19]2)(=O)=O)C=CC=CC=1>>[CH3:1][CH:2]1[CH2:7][CH2:6][CH:5]([NH:8][C:29]2[N:28]=[C:27]([C:20]3[C:21]4[C:22](=[N:23][CH:24]=[CH:25][CH:26]=4)[NH:18][CH:19]=3)[CH:32]=[CH:31][N:30]=2)[CH2:4][CH2:3]1

Participants

Reactant 2

HCID 806044-Methylcyclohexylamine

HCID 59596028HCID 59596028, compound

Product 1

HCID 58692228HCID 58692228, compoundYield 30.2%

Procedure

Using the procedure of example 1, 4-methylcyclohexylamine (92 mg) was reacted with compound 1f (100 mg) to provide compound 17 (25 mg, 30%) as a mixture of cis- and trans-isomers. 1H NMR (400 MHz, CDCl3) δ 8.94 (d, J=8.0 Hz, 1H), 8.92 (d, J=8.0 Hz, 1H), 8.28 (m, 2H), 8.20 (s, 1H), 8.19 (s, 1H), 8.14 (d, J=5.2 Hz, 1H), 8.11 (d, J=5.2 Hz, 1H), 7.25 (m, 2H), 7.03 (d, J=5.6 Hz, 1H), 7.00 (d, J=5.6 Hz, 1H), 4.15 (m, 1H), 3.83 (m, 1H), 2.15 (m, 2H), 1.89-1.14 (m, 16H), 1.01 (d, J=6.4 Hz, 3H), 0.98 (d, J=6.4 Hz, 3H). MS (ESI) m/z: 308 (M+H)+.

Sources & evidence

ORD record: ord-46b1630122fa46df9a6808ae2bf77023
Source dataset: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07855205B2

Reaction notes

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