Potassium Carbonate → 10-{4-[3-(2-methyl-pyrrolidin-1-yl)-propoxy]-phenyl}-6,7,8,9-tetrahydro-5H-1,4,10a-triaza-cyclohepta[f]indene

HRID 2251107Notes

Reaction equation

Cl[CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[N:13]3[C:17]([N:18]=[C:19]4[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][C:20]=24)=[CH:16][CH:15]=[N:14]3)=[CH:8][CH:7]=1.[CH3:26][CH:27]1[CH2:31][CH2:30][CH2:29][NH:28]1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.CCOC(C)=O>[CH3:26][CH:27]1[CH2:31][CH2:30][CH2:29][N:28]1[CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[N:13]3[C:17]([N:18]=[C:19]4[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][C:20]=24)=[CH:16][CH:15]=[N:14]3)=[CH:8][CH:7]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 10-[4-(3-chloro-propoxy)-phenyl]-6,7,8,9-tetrahydro-5H-1,4,10a-triaza-cyclohepta[f]indene (50 mg, 0.2 mmol), 2-methyl-pyrrolidine (71 mg, 1.0 mmol) and K2CO3 (45 mg, 0.3 mmol) in DMF (1 mL) was stirred at 80° C. overnight. The reaction was cooled, diluted with EtOAc (3 mL) and washed with H2O, brine, dried over MgSO4, and concentrated. The residue was purified by preparative LCMS to give 10-{4-[3-(2-methyl-pyrrolidin-1-yl)-propoxy]-phenyl}-6,7,8,9-tetrahydro-5H-1,4,10a-triaza-cyclohepta[f]indene (33 mg, 66% yield).

Workup

temperatureThe reaction was cooled
washwashed with H2O, brine
dry with materialdried over MgSO4
concentrationconcentrated
customThe residue was purified by preparative LCMS

Sources & evidence

ORD record: ord-7d98d8e99dad43b6be37527bb23b6466
Source dataset: uspto-grants-2008_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07319103B2

Reaction notes

Loading…