Hydrochloric Acid → HCID 57687104, compound

HRID 908492Notes

Reaction equation

Cl.[NH2:2][C:3]1[N:8]=[CH:7][C:6]([C:9]2[CH:10]=[N:11][N:12]([CH:14]3[CH2:19][CH2:18][N:17](C(OC(C)(C)C)=O)[CH2:16][CH2:15]3)[CH:13]=2)=[CH:5][C:4]=1[C:27]1[O:28][C:29]2[C:35]([C:36](=[O:39])[NH:37][CH3:38])=[CH:34][CH:33]=[CH:32][C:30]=2[N:31]=1>C(O)(C)C>[NH2:2][C:3]1[C:4]([C:27]2[O:28][C:29]3[C:35]([C:36]([NH:37][CH3:38])=[O:39])=[CH:34][CH:33]=[CH:32][C:30]=3[N:31]=2)=[CH:5][C:6]([C:9]2[CH:10]=[N:11][N:12]([CH:14]3[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]3)[CH:13]=2)=[CH:7][N:8]=1

Participants

Conditions

Temperature: 75 °C

Procedure

A 5M solution of hydrogen chloride in isopropanol (0.773 ml) was added to tert-butyl 4-[4-[6-amino-5-[7-(methylcarbamoyl)-1,3-benzoxazol-2-yl]-3-pyridyl]pyrazol-1-yl]piperidine-1-carboxylate (200 mg) dissolved in isopropanol (5 ml). The resulting solution was heated at 75° C. for 2 hours. The mixture was evaporated to dryness, diisopropylethyamine (1 ml) was added and the mixture was adsorbed on silica gel with 7N methanolic ammonia and dichloromethane. The crude product was purified by flash chromatography on silica gel eluting with 2 to 8% methanolic ammonia (7 N) in dichloromethane. The solvent was evaporated to dryness to afford 2-[2-amino-5-[1-(4-piperidyl)pyrazol-4-yl]-3-pyridyl]-N-methyl-1,3-benzoxazole-7-carboxamide (92 mg) as a solid.

Workup

customThe mixture was evaporated to dryness, diisopropylethyamine (1 ml)
additionwas added
customThe crude product was purified by flash chromatography on silica gel eluting with 2 to 8% methanolic ammonia (7 N) in dichloromethane
customThe solvent was evaporated to dryness

Sources & evidence

ORD record: ord-79cdec8c592f4d02b836ca6fc3beaa17
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08017611B2

Reaction notes

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