2-(2-(2-Hydroxyethoxy)ethoxy)ethyl 4-methylbenzenesulfonate → 4-(benzo[4,5]imidazo[1,2-a]pyrimidin-2-yl)-N-(2-(2-(2-fluoroethoxy)ethoxy)ethyl)aniline

HRID 452331Notes

Reaction equation

HRID 452331 reaction equation
N1C2N(C3C=CC=CC=3N=2)C=CC=1C1C=CC(NC[CH2:13][CH2:14][F:15])=CC=1.[N:25]1[C:26]2[N:27]([C:38]3[CH:44]=[CH:43][CH:42]=[CH:41][C:39]=3[N:40]=2)[CH:28]=[CH:29][C:30]=1[C:31]1[CH:37]=[CH:36][C:34]([NH2:35])=[CH:33][CH:32]=1.CC1C=CC(S([O:55][CH2:56][CH2:57][O:58][CH2:59][CH2:60]OCCO)(=O)=O)=CC=1>>[N:25]1[C:26]2[N:27]([C:38]3[CH:44]=[CH:43][CH:42]=[CH:41][C:39]=3[N:40]=2)[CH:28]=[CH:29][C:30]=1[C:31]1[CH:32]=[CH:33][C:34]([NH:35][CH2:60][CH2:59][O:58][CH2:57][CH2:56][O:55][CH2:13][CH2:14][F:15])=[CH:36][CH:37]=1

Participants

4

Reactant 3

HCID 109137352-(2-(2-Hydroxyethoxy)ethoxy)ethyl 4-methylbenzenesulfonateHCID 533408694-(Benzo[4,5]imidazo[1,2-a]pyrimidin-2-yl)-N-(3-fluoropropyl)anilineHCID 58362416HCID 58362416, compound

Product 1

HCID 583625154-(benzo[4,5]imidazo[1,2-a]pyrimidin-2-yl)-N-(2-(2-(2-fluoroethoxy)ethoxy)ethyl)aniline

Procedure

4-(benzo[4,5]imidazo[1,2-a]pyrimidin-2-yl)-N-(2-(2-(2-fluoroethoxy)ethoxy)ethyl)aniline was prepared using the procedure for 4-(Benzo[4,5]imidazo[1,2-a]pyrimidin-2-yl)-N-(3-fluoropropyl)aniline from 4-(benzo[4,5]imidazo[1,2-a]pyrimidin-2-yl)aniline (10 mg, 0.038 mmol) and 2-(2-(2-hydroxyethoxy)ethoxy)ethyl 4-methylbenzenesulfonate (23 mg, 0.075 mmol). The product T557 was obtained as a yellow solid (1.2 mg, 5.1%). 1H NMR (400 MHz, CDCl3): δ 9.31 (d, J=7.6 Hz, 1H), 8.25 (m, 2H), 8.02 (d, J=7.2 Hz, 1H), 7.78-7.75 (m, 1H), 7.72 (m, 1H), 7.61 (m, 1H), 6.80 (d, J=9.2 Hz, 2H), 4.56 (m, 1H), 4.45 (m, 1H), 3.75 (m, 1H), 3.71 (t, J=5.2 Hz, 2H), 3.69-3.65 (m, H), 3.47-3.43 (m, H); MS (ESI): 395 (M+H+).

Sources & evidence

ORD record
ord-3e0348f26da149af89d326b4d4b3b607
Source dataset
uspto-grants-2013_07
Patent number
US08491869B2

Reaction notes

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