Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Dimethylformamide | HCID 6228 | — |
| Reactant | 4-Methoxybenzoic Acid | HCID 7478 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) | HCID 9886157 | — |
| Reactant | Hydroxylamine monohydrate | HCID 22235265 | — |
| Reactant | (2-Chloro-4-morpholinothieno[3,2-d]pyrimidin-6-yl)methanamine | HCID 46180727 | — |
| Solvent | Sodium Bicarbonate | HCID 516892 | — |
| Product | HCID 59593015 | HCID 59593015 | 38% |
Reaction Steps
(2-Chloro-4-morpholinothieno[3,2-d]pyrimidin-6-yl)methanamine 27 from Example 11 (50.0 mg, 0.17 mM) was dissolved in 1.5 mL DMF. To this was added 77.6 mg (3.0 eq) of p-anisic acid, 129.3 mg (2.0 eq) HATU and 0.18 uL (6.0 eq) DIPEA and the reaction heated at 40° C. for 18 hours. Complete reaction was confirmed by HPLC and 2.0 eq NH2OH—H2O was added to the cooled reaction and the reaction stirred for ten minutes. The reaction was diluted with sat. NaHCO3, extracted with EtOAc, washed with brine, dried over MgSO4 and concentrated in vacuo. This intermediate was purified by flash chromatography (EtOAc/Hexanes) followed by Suzuki coupling of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)1H-indazole 7 as per General Procedure A. Complete reaction was confirmed by LCMS and the reaction was concentrated in vacuo to give 18.9 mg of 363 after RP-HPLC purification (38% yield). MS (Q1) 501.3 (M)+
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US07846929B2 |
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| Source dataset | uspto-grants-2010_12 |
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| ORD ID | ord-e43c503a96b94a4e8bb064ada4e31e45 |
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| Source note | uspto-grants-2010_12 |
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