1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 178500660, compound

HRID 1713749Notes

Reaction equation

[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([N:7]=[C:8]=S)[CH:2]=1.[NH:10]([C:12](=[O:33])[C:13]([NH:15][C:16]1[CH:21]=[CH:20][C:19]([C@H:22]2[CH2:27][CH2:26][C@H:25]([CH2:28][C:29]([O:31][CH3:32])=[O:30])[CH2:24][CH2:23]2)=[CH:18][CH:17]=1)=[O:14])[NH2:11].CCN=C=NCCCN(C)C>CC#N>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([NH:7][C:8]2[O:33][C:12]([C:13]([NH:15][C:16]3[CH:21]=[CH:20][C:19]([C@H:22]4[CH2:27][CH2:26][C@H:25]([CH2:28][C:29]([O:31][CH3:32])=[O:30])[CH2:24][CH2:23]4)=[CH:18][CH:17]=3)=[O:14])=[N:10][N:11]=2)[CH:2]=1

Participants

Conditions

Temperature: 80 °C

Procedure

3-Pyridyl isothiocyanate (41 mg, 0.3 mmol) was added in one portion to a suspension of methyl [trans-4-(4-{[hydrazino(oxo)acetyl]amino}-phenyl)cyclohexyl]acetate (Intermediate 43, 100 mg, 0.3 mmol) in CH3CN (5 mL) and the reaction mixture was heated at 80° C. for 10 minutes in the microwave and then cooled to room temperature. EDCI (58 mg, 0.3 mmol) was added in one portion and the reaction mixture was heated to 90° C. for 20 minutes. The mixture was cooled to room temperature and filtered to leave a solid. The solid was washed with CH3CN (5 mL) to give the title compound (90 mg, 69%) as a solid; 1H NMR δ 1.12-1.18 (2H, m), 1.45 (2H, q), 1.80 (5H, m), 2.24-2.26 (2H, d), 2.42-2.48 (1H, m), 3.61 (3H, s), 7.23 (2H, d), 7.43-7.46 (1H, m), 7.69-7.71 (2H, m), 8.06-8.09 (1H, m), 8.28-8.29 (1H, m), 8.78 (1H, d), 10.95 (1H, s), 11.22 (1H, s); MS m/e MH+ 436.

Workup

temperaturecooled to room temperature
temperaturethe reaction mixture was heated to 90° C. for 20 minutes
temperatureThe mixture was cooled to room temperature
filtrationfiltered
customto leave a solid
washThe solid was washed with CH3CN (5 mL)

Sources & evidence

ORD record: ord-94fc1994f91b4a74b1ff2cd5e35835e3
Source dataset: uspto-grants-2010_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07795283B2

Reaction notes

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