HCID 71515662, compound → HCID 71516118, compound

HRID 574650Notes

Reaction equation

[C:1]([N:4]1[CH2:9][CH2:8][C:7]2[N:10]([C@@H:21]3[C:29]4[C:24](=[C:25](Br)[CH:26]=[C:27]([F:30])[CH:28]=4)[CH2:23][C@H:22]3[OH:32])[N:11]=[C:12]([C:13]3[CH:14]=[C:15]([CH:18]=[CH:19][CH:20]=3)[C:16]#[N:17])[C:6]=2[CH2:5]1)(=[O:3])[CH3:2].[C:33]([Cu])#[N:34]>CS(C)=O>[C:1]([N:4]1[CH2:9][CH2:8][C:7]2[N:10]([C@@H:21]3[C:29]4[CH:28]=[C:27]([F:30])[CH:26]=[C:25]([C:33]#[N:34])[C:24]=4[CH2:23][C@H:22]3[OH:32])[N:11]=[C:12]([C:13]3[CH:20]=[CH:19][CH:18]=[C:15]([C:16]#[N:17])[CH:14]=3)[C:6]=2[CH2:5]1)(=[O:3])[CH3:2]

Participants

Conditions

Temperature: 180 °C

Procedure

According to Scheme 15: A mixture of 3-[5-acetyl-1-((1R,2R)-4-bromo-6-fluoro-2-hydroxy-indan-1-yl)-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-c]pyridin-3-yl]-benzonitrile (11d) (0.15 g, 0.303 mmol) and CuCN (54 mg, 0.606 mmol) in dimethylsulfoxide (2 ml) was stirred at 180° C. for 90 min under microwave irradiation. The mixture was purified by reverse phase HPLC (CH3CN/water gradient with 0.1% trifluoroacetic acid) to give 27 mg of (1R,2R)-1-[5-acetyl-3-(3-cyano-phenyl)-4,5,6,7-tetrahydro-pyrazolo[4,3-c]pyridin-1-yl]-6-fluoro-2-hydroxy-indan-4-carbonitrile (21b). Rt=1.16 min (LC method 4). Detected mass: 442.12 [M+H+].

Workup

customThe mixture was purified by reverse phase HPLC (CH3CN/water gradient with 0.1% trifluoroacetic acid)

Sources & evidence

ORD record: ord-750154ff1e244ac9935a2f0470b29752
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09034897B2

Reaction notes

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