Dimethylacetamide → HCID 71510901, compound

HRID 1499731Notes

Reaction equation

[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]2[N:8]([CH:12]([C:14]3[C:15]([O:35][CH3:36])=[C:16]([C:22]4[CH:27]=[CH:26][N:25]=[C:24]([C:28]([N:30]([CH2:32][CH2:33][OH:34])[CH3:31])=[O:29])[CH:23]=4)[C:17]([CH3:21])=[C:18](Cl)[CH:19]=3)[CH3:13])[N:9]=[C:10]([CH3:11])[C:3]=12.[CH3:37][N:38](C)C(=O)C>[Zn].[C-]#N.[Zn+2].[C-]#N>[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]2[N:8]([CH:12]([C:14]3[C:15]([O:35][CH3:36])=[C:16]([C:22]4[CH:27]=[CH:26][N:25]=[C:24]([C:28]([N:30]([CH2:32][CH2:33][OH:34])[CH3:31])=[O:29])[CH:23]=4)[C:17]([CH3:21])=[C:18]([C:37]#[N:38])[CH:19]=3)[CH3:13])[N:9]=[C:10]([CH3:11])[C:3]=12

Participants

Conditions

Temperature: 120 °C

Procedure

The above catalyst (0.05 mL) was added to a mixture of 4-{3-[1-(4-amino-3-methyl-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-5-chloro-2-methoxy-6-methylphenyl}-N-(2-hydroxyethyl)-N-methylpyridine-2-carboxamide (from Example 19) (4.0 mg, 0.0078 mmol), zinc (0.22 mg, 0.0034 mmol) and zinc cyanide (0.92 mg, 0.0078 mmol) in N,N-dimethylacetamide (0.1 mL). The mixture was degassed and then the reaction was heated at 120° C. for 1.5 hours. The crude mixture was applied on RP-HPLC (XBridge C18 column, eluting with a gradient of acetonitrile/water containing 0.1% ammonium hydroxide, at flow rate of 30 mL/min) to give the desired product. The product was isolated as a racemic mixture. LCMS calculated for C26H29N8O3 (M+H)+: m/z=501.2; Found: 501.2

Workup

customThe mixture was degassed
washeluting with a gradient of acetonitrile/water containing 0.1% ammonium hydroxide, at flow rate of 30 mL/min)

Sources & evidence

ORD record: ord-9d1ca5934e3945239847cc015c2a512f
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09199982B2

Reaction notes

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