HCID 136951802, compound → HCID 136493144, compound

HRID 2200389Notes

Reaction equation

[F:1][C:2]1[CH:7]=[C:6](I)[CH:5]=[CH:4][C:3]=1[N:9]1[CH2:14][CH2:13][N:12]([C@@H:15]2[CH2:19][CH2:18][C:17]([C:20]3[NH:29][C:28](=[O:30])[C:27]4[CH2:26][C:25]5([CH2:32][CH2:31]5)[CH2:24][CH2:23][C:22]=4[N:21]=3)=[CH:16]2)[CH2:11][CH2:10]1.[C:33]([Zn]C#N)#[N:34]>CN(C)C=O>[F:1][C:2]1[CH:7]=[C:6]([CH:5]=[CH:4][C:3]=1[N:9]1[CH2:14][CH2:13][N:12]([C@@H:15]2[CH2:19][CH2:18][C:17]([C:20]3[NH:29][C:28](=[O:30])[C:27]4[CH2:26][C:25]5([CH2:32][CH2:31]5)[CH2:24][CH2:23][C:22]=4[N:21]=3)=[CH:16]2)[CH2:11][CH2:10]1)[C:33]#[N:34]

Participants

Conditions

Temperature: 117.5 °C

Procedure

To a stirred solution of (R)-2′-(3-(4-(2-fluoro-4-iodophenyl)piperazin-1-yl)cyclopent-1-en-1-yl)-7′,8′-dihydro-3′H-spiro[cyclopropane-1,6′-quinazolin]-4′(5′H)-one (synthesis from (R)-3-aminocyclopent-1-enecarbonitrile and 2-fluoro-4-iodoaniline as described in example 11) (0.160 g, 0.293 mmol) in N,N-dimethylformamide (10 ml) was added dicyanozinc (0.344 g, 2.93 mmol) at 25° C. The reaction mixture was heated to 115-120° C. for 4 h. Progress of the reaction was monitored by TLC. After completion of reaction, reaction mixture was cooled and solvent was evaporated under reduced pressure to obtain crude product. Crude product was purified by flash column chromatography over silica gel (110-200 mesh) using 6% methanol in in dichloromethane as eluent to obtain title compound (0.045 g, 34.5%).

Workup

customAfter completion of reaction, reaction mixture
temperaturewas cooled
customsolvent was evaporated under reduced pressure
customto obtain crude product
customCrude product was purified by flash column chromatography over silica gel (110-200 mesh)

Sources & evidence

ORD record: ord-8804a964cfbd498593bd8bb0f74d4f9c
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09359367B2

Reaction notes

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