Cyclohexylamine → HCID 23435659, compound

HRID 1375644Notes

Reaction equation

Br[C:2]1[CH:7]=[C:6]([C:8]2[C:9]([C:16]3[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=3)=[N:10][O:11][C:12]=2[CH2:13][O:14][CH3:15])[CH:5]=[CH:4][N:3]=1.[CH:23]1([NH2:29])[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1.C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.CC([O-])(C)C.[Na+]>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O>[CH:23]1([NH:29][C:2]2[CH:7]=[C:6]([C:8]3[C:9]([C:16]4[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=4)=[N:10][O:11][C:12]=3[CH2:13][O:14][CH3:15])[CH:5]=[CH:4][N:3]=2)[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1

Participants

Conditions

Temperature: 80 °C

Procedure

To a stirred solution of the above Compound 19b (20 mg, 0.050 mmol), cyclohexylamine (11 μL, 0.13 mmol), and BINAP (4.7 mg, 0.0075 mmol) in toluene (0.4 mL) at 25° C. was added Pd2(dba)3 (2.3 mg, 0.0025 mmol) followed by NaOtBu (12 mg, 0.13 mmol). The solution was heated to 80° C. for 15 h. The solution was cooled, poured into H2O (5 mL), extracted with EtOAc (4×5 mL), dried (MgSO4), filtered and concentrated. HPLC (gradient elution, 90–10% H2O—CH3CN) provided the title compound (9.1 mg, 0.022 mmol, 44%).

Workup

temperatureThe solution was cooled
extractionextracted with EtOAc (4×5 mL)
dry with materialdried (MgSO4)
filtrationfiltered
concentrationconcentrated
washHPLC (gradient elution, 90–10% H2O—CH3CN)

Sources & evidence

ORD record: ord-56908b2e36d24ad9811de9b1f8aaf5e9
Source dataset: uspto-grants-2007_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07169798B2

Reaction notes

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