Potassium Carbonate → 1-(2-(4-(5-(Thiophen-2-yl)thiophen-2-yl)pyrimidin-2-ylamino)ethyl)-1H-benzo[d]imidazol-2(3H)-one

HRID 2267297Notes

Reaction equation

Cl[C:2]1[N:7]=[C:6]([C:8]2[S:9][C:10]([C:13]3[S:14][CH:15]=[CH:16][CH:17]=3)=[CH:11][CH:12]=2)[CH:5]=[CH:4][N:3]=1.Cl.[NH2:19][CH2:20][CH2:21][N:22]1[C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=2[NH:24][C:23]1=[O:31].C(=O)([O-])[O-].[K+].[K+]>CN1CCCC1>[S:14]1[CH:15]=[CH:16][CH:17]=[C:13]1[C:10]1[S:9][C:8]([C:6]2[CH:5]=[CH:4][N:3]=[C:2]([NH:19][CH2:20][CH2:21][N:22]3[C:26]4[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=4[NH:24][C:23]3=[O:31])[N:7]=2)=[CH:12][CH:11]=1

Participants

Conditions

Temperature: 160 °C

Procedure

A mixture of 2-chloro-4-(5-(thiophen-2-yl)thiophen-2-yl)pyrimidine (20 mg, 0.072 mmol), 1-(2-aminoethyl)-1H-benzo[d]imidazol-2(3H)-one hydrochloride salt (15 mg, 0.072 mmol) and potassium carbonate (20 mg, excess) in N-methylpyrrolidine (1 mL) was heated at 160° C. for 35 min in a Personal Chemistry microwave reactor. The solvent was removed in vacuo and the product was purified by HPLC to give the title compound (trifluoroacetate salt) as a yellow solid. MS (M+H)+ 420.

Workup

customThe solvent was removed in vacuo
customthe product was purified by HPLC

Sources & evidence

ORD record: ord-26f7f6a01dfe450a90d790368ff68c62
Source dataset: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07858785B2

Reaction notes

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