HuagongsheHuagongshe Chemistry Print Report · For research reference only
Acetic Acid → HCID 67219251, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Acetic Acid | HCID 176 | — |
| Reactant | 2,5-Difluorobenzaldehyde | HCID 137663 | — |
| Reactant | Sodium cyanoborohydride | HCID 5003444 | — |
| Reactant | (4-Amino-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-(3-amino-phenyl)methanone | HCID 11859044 | — |
| Solvent | Methanol | HCID 887 | — |
| Product | HCID 67219251 | HCID 67219251 | 58% |
Reaction Steps
2,5-difluorobenzaldehyde (88.1 mg, 0.62 mmol) was added to a solution of (4-Amino-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-(3-amino-phenyl)-methanone (100 mg, 0.31 mmol) and AcOH (18.6 mg, 0.31 mmol) in MeOH (10 mL). After 5 min NaCNBH3 was added. After 3 h the reaction was quenched with 1N NaOH. The aqueous layer was extracted with EtOAc (2×). The combined organic layers were washed with water, dried over MgSO4, and concentrated. Purification by flash column chromatography (CH2Cl2/MeOH 98:2) afforded the title compound as a white solid (80 mg, 58%). MS: 448.1 (MH+); HPLC Rf: 6.59 min. (HPLC method 4).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07271262B2 |
| Source dataset | uspto-grants-2007_09 |
| ORD ID | ord-5d2dd7574ebc4aaa8f7a5cd5312f665f |
| Source note | uspto-grants-2007_09 |