Cyclohexylamine → HCID 178493707, compound

HRID 2089052Notes

Reaction equation

HRID 2089052 reaction equation
Cl[CH2:2][C:3]([NH:5][C@H:6]1[CH2:11][CH2:10][C@H:9]([NH:12][C:13]2[CH:18]=[C:17]([C:19]3[C:27]4[C:22](=[N:23][CH:24]=[C:25]([O:28][CH3:29])[CH:26]=4)[NH:21][CH:20]=3)[CH:16]=[C:15]([Cl:30])[N:14]=2)[CH2:8][CH2:7]1)=[O:4].[CH:31]1([NH2:37])[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]1.C(N(CC)CC)C>CN(C=O)C>[Cl:30][C:15]1[N:14]=[C:13]([NH:12][C@H:9]2[CH2:10][CH2:11][C@H:6]([NH:5][C:3](=[O:4])[CH2:2][NH:37][CH:31]3[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]3)[CH2:7][CH2:8]2)[CH:18]=[C:17]([C:19]2[C:27]3[C:22](=[N:23][CH:24]=[C:25]([O:28][CH3:29])[CH:26]=3)[NH:21][CH:20]=2)[CH:16]=1

Participants

5

Reactant 3

HCID 7965CyclohexylamineHCID 8471TriethylamineHCID 178493706HCID 178493706, compound

Product 1

HCID 178493707HCID 178493707, compoundYield 77.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of Example 251a (50.0 mg, 0.112 mmol), cyclohexanamine (0.038 mL, 0.335 mmol) and triethylamine (0.054 mL, 0.39 mmol) in DMF (1.0 mL) was stirred at 60° C. for 2.5 hours. The reaction mixture was concentrated and purified by reverse-phase HPLC as described in Example 56 to give the title compound (44.6 mg) as trifluoroacetic acid salts. 1H NMR (400 MHz, CD3OD) ppm 1.20-1.53 (m, 9H), 1.72 (m, 1H), 1.83-1.95 (m, 2H), 1.98-2.25 (m, 6H), 3.07 (m, 1H), 3.67-3.84 (m, 4H), 3.96 (s, 3H), 6.80 (d, J=1.53 Hz, 1H), 6.89 (d, J=1.22 Hz, 1H), 7.87-7.94 (m, 2H), 8.08 (d, J=2.44 Hz, 1H). MS (DCI+) m/z 511.3 (M+H)+.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. custompurified by reverse-phase HPLC

Sources & evidence

ORD record
ord-e397a1ed2aac49d6995079b223a692d2
Source dataset
uspto-grants-2013_05
Patent number
US08435980B2

Reaction notes

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