Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Formaldehyde | HCID 712 | — |
| Reactant | Sodium cyanoborohydride | HCID 5003444 | — |
| Reactant | HCID 69311654 | HCID 69311654 | — |
| Catalyst | Acetic Acid | HCID 176 | — |
| Solvent | Methanol | HCID 887 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Solvent | Sodium Bicarbonate | HCID 516892 | — |
| Product | HCID 69308811 | HCID 69308811 | 618.1% |
Reaction Steps
To a solution of ethyl 5-[4-(5-amino-3-pyridinyl)-7-ethyl-2-methylpyrrolo[1,2-b]pyridazin-3-yl]pentanoate (55 mg), 37% formaldehyde solution (277 mg) and sodium cyanoborohydride (273 mg) in acetnitrile (1 mL) and methanol (1 mL) was added acetic acid (2 drops) and the mixture was stirred at ambient temperature for 2 hours. The solution was diluted with saturated sodium bicarbonate solution and extracted with chloroform. The organic layer was washed with brine, dried over magnesium sulfate, and evaporated in vacuo. The residue was purified by preparative silica gel column chromatography eluting with a mixture of chloroform and methanol (20:1) to give ethyl 5-{4-[5-(dimethylamino)-3-pyridinyl]-7-ethyl-2-methylpyrrolo[1,2-b]pyridazin-3-yl}pentanoate as yellow oil (365 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07317009B2 |
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| Source dataset | uspto-grants-2008_01 |
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| ORD ID | ord-f238a61ee79e4ee8b62a28b542a5a718 |
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| Source note | uspto-grants-2008_01 |
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