Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | 4-Nitrophenethylamine | HCID 95153 | — |
| Reactant | HCID 53317887 | HCID 53317887 | — |
| Solvent | Ethanol | HCID 702 | — |
| Solvent | Diethyl Ether | HCID 3283 | — |
| Product | HCID 69066223 | HCID 69066223 | 66% |
Reaction Steps
By proceeding in a similar manner to Example 43(b) but substituting 2-(6-methoxy-1H-indol-3-yl)-ethylamine for 2-(4-nitro-phenyl)-ethylamine, and substituting acetonitrile for EtOH as solvent in Step 3 there is prepared [2-(6-methoxy-1H-indol-3-yl)-ethyl]-[2-methoxy-6-(3-methoxy-phenyl)-pyrimidin-4-yl]-amine which is dissolved in ether and treated with 1 M hydrogen chloride in ether affording [2-(6-methoxy-1H-indol-3-yl)-ethyl]-[2-methoxy-6-(3-methoxy-phenyl)-pyrimidin-4-yl]-amine hydrochloride [58.6 mg, 66%, Example 43(g)] as a solid. LC/MS: RT=2.48 minutes MS: 405 (M+H). 1H NMR [300 MHz, (CD3)2SO]: □10.6 (1H, s), 7.3-7.5 (4H, m), 7.12 (1H, m), 7.02 (1H, m), 6.8 (1H, s), 6.61 (2H, m), 3.99 (3H, s), 3.8 (3H, s), 3.72 (3H, s), 3.58 (2H, m), 2.94 (2H, m). IC50=104 nM
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07517889B2 |
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| Source dataset | uspto-grants-2009_04 |
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| ORD ID | ord-40eb098360874e2ea43205c41cf55c14 |
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| Source note | uspto-grants-2009_04 |
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