Triethylamine → Tert-butyl 2-(3-(3-cyclohexylthioureido)phenoxy)ethylcarbamate

HRID 716752Notes

Reaction equation

[N:1]([CH:4]1[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]1)=[C:2]=[S:3].[NH2:10][C:11]1[CH:12]=[C:13]([CH:25]=[CH:26][CH:27]=1)[O:14][CH2:15][CH2:16][NH:17][C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21].CCN(CC)CC>CN(C1C=CN=CC=1)C.C1COCC1>[CH:4]1([NH:1][C:2](=[S:3])[NH:10][C:11]2[CH:12]=[C:13]([CH:25]=[CH:26][CH:27]=2)[O:14][CH2:15][CH2:16][NH:17][C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]1

Participants

Conditions

Temperature: 50 °C

Procedure

A mixture of isothiocyanatocyclohexane (27) (0.16 mL, 1.17 mmol), tert-butyl 2-(3-aminophenoxy)ethylcarbamate (3) (0.282 g, 1.12 mmol), DMAP (0.024 g, 0.196 mmol) and Et3N (0.3 mL, 2.15 mmol) in anhydrous THF was stirred under argon at 50° C. for 24 h. The mixture was concentrated under reduced pressure. Purification by flash chromatography (30% to 60% EtOAc—hexanes gradient) gave tert-butyl 2-(3-(3-cyclohexylthioureido)phenoxy)ethylcarbamate (28) as a white solid. Yield (0.1917 g, 44%); 1H NMR (400 MHz, DMSO-d6) δ 9.29 (s, 1H), 7.59 (br.d, J=7.6 Hz, 1H), 7.15 (t, J=8.2 Hz, 1H), 6.97 (br.t, J=5.5 Hz, 1H), 6.85-6.89 (m, 1H), 6.58-6.63 (m, 1H), 4.06 (br.s, 1H), 3.88 (t, J=5.9 Hz, 2H), 3.25 (q, J=5.7 Hz, 2H), 1.82-1.90 (m, 2H), 1.60-1.70 (m, 2H), 1.47-1.57 (m, 1H), 1.36 (s, 9H), 1.07-1.34 (m, 6H).

Workup

concentrationThe mixture was concentrated under reduced pressure
customPurification by flash chromatography (30% to 60% EtOAc—hexanes gradient)

Sources & evidence

ORD record: ord-8c0807bd757940849271b5f3f48147d3
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09193669B2

Reaction notes

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