Diisopropylethylamine → HCID 69034747, compound

HRID 854259Notes

Reaction equation

[CH2:1]([O:3][C:4](=[O:19])[CH2:5][CH2:6][CH2:7][N:8]1[C:12]2[N:13]=[C:14]([CH3:18])[N:15]=[C:16](Cl)[C:11]=2[CH:10]=[CH:9]1)[CH3:2].[C:20]([O:24][C:25](=[O:40])[C@H:26]([CH2:38][SH:39])[NH:27][S:28]([C:31]1[CH:36]=[CH:35][C:34]([Br:37])=[CH:33][CH:32]=1)(=[O:30])=[O:29])([CH3:23])([CH3:22])[CH3:21].CCN(C(C)C)C(C)C>CN1C(=O)CCC1>[CH2:1]([O:3][C:4](=[O:19])[CH2:5][CH2:6][CH2:7][N:8]1[C:12]2[N:13]=[C:14]([CH3:18])[N:15]=[C:16]([S:39][CH2:38][C@H:26]([NH:27][S:28]([C:31]3[CH:36]=[CH:35][C:34]([Br:37])=[CH:33][CH:32]=3)(=[O:29])=[O:30])[C:25]([O:24][C:20]([CH3:22])([CH3:23])[CH3:21])=[O:40])[C:11]=2[CH:10]=[CH:9]1)[CH3:2]

Participants

Conditions

Temperature: 100 °C

Procedure

279 mg of 4-(4-chloro-2-methyl-pyrrolo[2,3-d]pyrimidin-7-yl)-butyric acid ethyl ester (example 2a) and 655 mg of N-(4-bromobenzenesulfonyl)-(R)-cysteine-tert-butyl ester (example 6b) were dissolved in 2 ml of NMP and 0.68 ml of DIPEA were added. The reaction mixture was heated to 100° C. for 4 h. The mixture was diluted with 60 ml of EE and extracted with 10% citric acid, saturated NaCl solution and with water. The organic phase was dried over MgSO4 and the solvent was removed in vacuo. The crude product was chromatographed on silica gel eluting with EE/toluene (1:6). Yield: 108 mg.

Workup

additionThe mixture was diluted with 60 ml of EE
extractionextracted with 10% citric acid, saturated NaCl solution and with water
dry with materialThe organic phase was dried over MgSO4
customthe solvent was removed in vacuo
customThe crude product was chromatographed on silica gel eluting with EE/toluene (1:6)

Sources & evidence

ORD record: ord-774ca723c1db4ff2acb7aba3d033b0ee
Source dataset: uspto-grants-2007_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07259159B2

Reaction notes

Loading…