Bis(2-bromoethyl) ether → HCID 59190851, compound

HRID 418352Notes

Reaction equation

FC(F)(F)C(O)=O.[NH2:8][C@@H:9]1[CH2:40][CH2:39][C:12]2[N:13]=[C:14]([NH:16][C:17]([C:19]3[CH:20]=[C:21]([CH:36]=[CH:37][CH:38]=3)[CH2:22][NH:23][C:24](=[O:35])[C:25]3[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[C:27]([O:33][CH3:34])[CH:26]=3)=[O:18])[S:15][C:11]=2[CH2:10]1.CCN(C(C)C)C(C)C.Br[CH2:51][CH2:52][O:53][CH2:54][CH2:55]Br>CN(C=O)C>[CH3:34][O:33][C:27]1[CH:26]=[C:25]([CH:30]=[CH:29][C:28]=1[O:31][CH3:32])[C:24]([NH:23][CH2:22][C:21]1[CH:36]=[CH:37][CH:38]=[C:19]([C:17](=[O:18])[NH:16][C:14]2[S:15][C:11]3[CH2:10][C@H:9]([N:8]4[CH2:55][CH2:54][O:53][CH2:52][CH2:51]4)[CH2:40][CH2:39][C:12]=3[N:13]=2)[CH:20]=1)=[O:35]

Participants

Conditions

Temperature: 70 °C

Procedure

Dissolved N-[3-((R)-6-Amino-4,5,6,7-tetrahydro-benzothiazol-2-ylcarbamoyl)-benzyl]-3,4-dimethoxy-benzamide trifluoroacetate (50.0 mg, 0.09 mmol) in 1.5 mL of dry DMF. To this was added DIPEA (0.05 mL, 0.26 mmol) and the 1-bromo-2-(2-bromo-ethoxy)-ethane (0.02 mL, 0.12 mmol). The mixture was heated at 70° C. overnight. LC-MS analysis indicted the desired material. Dissolved in 5 mL of DMF and purified via prep HPLC (5%-95% CH3CN/H2O) to give the desired product with one major impurity. Applied to a SiO2 prep plate. Eluted with (10% MeOH/1% NH3/CH2Cl2) to give 18.9 mg of N-[3-((R)-6-Amino-4,5,6,7-tetrahydro-benzothiazol-2-ylcarbamoyl)-benzyl]-3,4-dimethoxy-benzamide. MS, electrospray 537.6 (M+H).

Workup

custompurified via prep HPLC (5%-95% CH3CN/H2O)

Sources & evidence

ORD record: ord-a101db3440724732a2c06d0fa57e2504
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08093266B2

Reaction notes

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