Hydrochloric Acid → HCID 66896698, compound

HRID 1913244Notes

Reaction equation

C[Si](C)(C)CCOC[N:7](COCC[Si](C)(C)C)[C:8]1[N:13]2[N:14]=[CH:15][C:16]([C:17]3[CH:18]=[N:19][C:20]4[C:25]([CH:26]=3)=[CH:24][CH:23]=[CH:22][CH:21]=4)=[C:12]2[N:11]=[C:10]([CH2:27][N:28]([CH:36]2[CH2:41][CH2:40][O:39][CH2:38][CH2:37]2)[C:29](=[O:35])[O:30][C:31]([CH3:34])([CH3:33])[CH3:32])[C:9]=1[C:42]([O:44]CC)=[CH2:43].Cl>O1CCOCC1>[C:42]([C:9]1[C:10]([CH2:27][N:28]([CH:36]2[CH2:41][CH2:40][O:39][CH2:38][CH2:37]2)[C:29](=[O:35])[O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[N:11][C:12]2[N:13]([N:14]=[CH:15][C:16]=2[C:17]2[CH:18]=[N:19][C:20]3[C:25]([CH:26]=2)=[CH:24][CH:23]=[CH:22][CH:21]=3)[C:8]=1[NH2:7])(=[O:44])[CH3:43]

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of tert-butyl (7-(bis((2-(trimethylsilyl)ethoxy)methyl)amino)-6-(1-ethoxyvinyl)-3-(quinolin-3-yl)pyrazolo[1,5-a]pyrimidin-5-yl)methyl(tetrahydro-2H-pyran-4-yl)carbamate (Int-8f, 35 mg), 4N HCl in dioxane (0.3 mL) and dioxane (2 mL) was heated at 60° C. for 10 min. Concentration afforded crude tert-butyl (6-acetyl-7-amino-3-(quinolin-3-yl)pyrazolo[1,5-a]pyrimidin-5-yl)methyl(tetrahydro-2H-pyran-4-yl)carbamate (Int-8g), which was then heated under microwave conditions with N2H4.H2O (200 uL) and NMP (1.5 mL) first at 100° C. for 30 min and then at 200° C. for 1h. Purification with prep-LC provided N-((3-methyl-6-(quinolin-3-yl)-1H-dipyrazolo[1,5-a:4′,3′-e]pyrimidin-4-yl)methyl)tetrahydro-2H-pyran-4-amine (26),

Workup

concentrationConcentration

Sources & evidence

ORD record: ord-27c1b2bb6a7c4b6ca08e4cecd8e45d01
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08609675B2

Reaction notes

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