1,1'-Carbonyldiimidazole → HCID 57586413, compound

HRID 2190347Notes

Reaction equation

[NH2:1][C:2]1[N:6]=[C:5]([C:7]2[CH:12]=[CH:11][C:10]([NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[CH:9][CH:8]=2)[S:4][N:3]=1.C1N=CN([C:26](N2C=NC=C2)=[O:27])C=1.[C:33]1([CH:39]([C:51]2[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=2)[CH2:40][CH2:41][NH:42][CH2:43][CH2:44][C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][N:46]=2)[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>CN(C1C=CN=CC=1)C.CN(C=O)C>[C:33]1([CH:39]([C:51]2[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=2)[CH2:40][CH2:41][N:42]([CH2:43][CH2:44][C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][N:46]=2)[C:26](=[O:27])[NH:1][C:2]2[N:6]=[C:5]([C:7]3[CH:8]=[CH:9][C:10]([NH:13][C:14](=[O:20])[O:15][C:16]([CH3:17])([CH3:19])[CH3:18])=[CH:11][CH:12]=3)[S:4][N:3]=2)[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1

Participants

Conditions

Temperature: 50 °C

Procedure

To a mixture of tert-butyl 4-(3-amino-1,2,4-thiadiazol-5-yl)phenylcarbamate (0.078 g, 0.27 mmol), DMAP (0.049 g, 0.40 mmol), and CDI (0.066 g, 0.41 mmol) was added DMF (1 mL). The reaction mixture was heated to 50° C. for 15 h and 3,3-diphenyl-N-(2-(pyridin-2-yl)ethyl)propan-1-amine (0.090 g, 0.28 mmol) was added. The reaction mixture was heated to 50° C. for 20 h. Direct purification by flash column chromatography on silica gel (eluted with 50% to 100% EtOAc in hexanes) gave tert-butyl 4-(3-(3-(3,3-diphenylpropyl)-3-(2-(pyridin-2-yl)ethyl)ureido)-1,2,4-thiadiazol-5-yl)phenylcarbamate 156.

Workup

temperatureThe reaction mixture was heated to 50° C. for 20 h
customDirect purification by flash column chromatography on silica gel (eluted with 50% to 100% EtOAc in hexanes)

Sources & evidence

ORD record: ord-2d92db52544b4afdbbb9f6c6df6ed392
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08324396B2

Reaction notes

Loading…