Ethyl cyanoacetate → HCID 86695130, compound

HRID 1503962Notes

Reaction equation

I[CH2:2][C@H:3]1[CH2:14][CH2:13][C:12]2[S:11][C:10]3[C:5](=[C:6]([O:15][CH:16]4[CH2:21][CH2:20][CH:19]([N:22]5[CH2:27][CH2:26][O:25][CH2:24][CH2:23]5)[CH2:18][CH2:17]4)[N:7]=[CH:8][N:9]=3)[C:4]1=2.C1OCCOCCOCCOCCOCCOC1.C(=O)([O-])[O-].[K+].[K+].[C:52]([CH2:54][C:55]([O:57][CH2:58][CH3:59])=[O:56])#[N:53]>C1C=CC=CC=1>[C:52]([CH:54]([CH2:2][C@H:3]1[CH2:14][CH2:13][C:12]2[S:11][C:10]3[C:5](=[C:6]([O:15][CH:16]4[CH2:21][CH2:20][CH:19]([N:22]5[CH2:27][CH2:26][O:25][CH2:24][CH2:23]5)[CH2:18][CH2:17]4)[N:7]=[CH:8][N:9]=3)[C:4]1=2)[C:55]([O:57][CH2:58][CH3:59])=[O:56])#[N:53]

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of (3S)-3-(iodomethyl)-12-[[4-(morpholin-4-yl)cyclohexyl]oxy]-7-thia-9,11-diazatricyclo[6.4.0.0[2,6]]dodeca-1(12),2(6),8,10-tetraene (287 mg, 0.57 mmol, 1.00 equiv), 18-Crown-6 (190 mg, 0.72 mmol, 1.25 equiv), potassium carbonate (141 mg, 1.02 mmol, 1.78 equiv) and ethyl 2-cyanoacetate (678 mg, 5.99 mmol, 10.43 equiv) in benzene (20 mL) was stirred overnight at 80° C. under nitrogen. After cooling to room temperature, the solvent was removed under vacuum and the residue was purified by a silica gel column with DCM/MeOH (30:1-10:1) to provide 230 mg (83%) of ethyl 2-cyano-3-[(3R)-12-[[4-(morpholin-4-yl)cyclohexyl]oxy]-7-thia-9,11-diazatricyclo[6.4.0.0[2,6]]dodeca-1(12),2(6),8,10-tetraen-3-yl]propanoate as a light yellow solid. MS (ES): m/z 485 [M+H]+.

Workup

temperatureAfter cooling to room temperature
customthe solvent was removed under vacuum
customthe residue was purified by a silica gel column with DCM/MeOH (30:1-10:1)

Sources & evidence

ORD record: ord-354738200d7d40d28134f8007ad75578
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09212190B2

Reaction notes

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