1,4-Diaminocyclohexane → HCID 178511658, compound

HRID 2264265Notes

Reaction equation

HRID 2264265 reaction equation
[CH2:1]1[CH:6]([NH2:7])[CH2:5][CH2:4][CH:3]([NH2:8])[CH2:2]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>>[NH:18]1[C:22]2=[N:23][CH:24]=[CH:25][CH:26]=[C:21]2[C:20]([C:27]2[CH:32]=[CH:31][N:30]=[C:29]([NH:7][C@H:6]3[CH2:5][CH2:4][C@H:3]([NH2:8])[CH2:2][CH2:1]3)[N:28]=2)=[CH:19]1

Participants

3

Reactant 2

HCID 183741,4-DiaminocyclohexaneHCID 59596028HCID 59596028, compound

Product 1

HCID 178511658HCID 178511658, compoundYield 34.5%

Procedure

Using the procedure of example 1, trans-1,4-cyclohexyldiamine (277 mg) was reacted with compound 1f (300 mg) to provide compound 42 (86 mg, 34%). 1H NMR (400 MHz, CD3OD) δ 8.90 (d, J=8.0 Hz, 1H), 8.25 (d, J=5.6 Hz, 1H), 8.17 (s, 1H), 8.12 (d, J=8.0 Hz, 1H), 7.22 (m, 1H), 6.95 (d, J=5.6 Hz, 1H), 3.85 (m, 1H), 2.78 (m, 1H), 2.18 (m, 2H), 2.20 (m, 2H), 1.40 (m, 4H). MS (ESI) m/z: 309 (M+H)+.

Sources & evidence

ORD record
ord-48be8ef451d14a60b44ef917abf9e6bb
Source dataset
uspto-grants-2010_12
Patent number
US07855205B2

Reaction notes

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