Acetonitrile → HCID 59993201, compound

HRID 238222Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([N:12]2[CH2:17][CH2:16][N:15]([CH2:18][C:19]3[NH:28][C:27](=[O:29])[C:26]4[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=4)[N:20]=3)[CH2:14][CH2:13]2)(=[O:11])=[O:10])=[CH:5][CH:4]=1.[CH:30]1(I)[CH2:34][CH2:33][CH2:32][CH2:31]1.C(=O)([O-])[O-].[K+].[K+].CC#N>CN(C=O)C>[CH:30]1([O:29][C:27]2[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[N:20]=[C:19]([CH2:18][N:15]3[CH2:14][CH2:13][N:12]([S:9]([C:6]4[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=4)(=[O:10])=[O:11])[CH2:17][CH2:16]3)[N:28]=2)[CH2:34][CH2:33][CH2:32][CH2:31]1

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of 2-[4-(4-Methoxy-benzenesulfonyl)-piperazin-1-ylmethyl]-3H-quinazolin-4-one (83 mg, 0.2 mmol), cyclopentyl iodide (46 μL, 0.4 mmol), and potassium carbonate (138 mg, 1 mmol) in DMF (1 mL) was heated to 90° C. for 1 day. The reaction mixture was partitioned between dichloromethane and water. The organic layer was concentrated in vacuo and the residue was purified by HPLC (in the absence of TFA) to yield the product. 1H NMR (400 MHz, CDCl3) δ 8.11 (d, J=8.1 Hz, 1H), 7.88 (d, J=8.4 Hz, 1H), 7.78 (t, J=7.6 Hz, 1H), 7.71 (d, J=8.8 Hz, 2H), 7.51 (t, J=7.5 Hz, 1H), 7.00 (d, J=8.8 Hz, 2H), 5.73 (quintet, J=3.0 Hz, 1H), 3.88 (m, 5H), 3.12 (m, 4H), 2.84 (m, 4H), 1.90 (m, 8H); HPLC ret. time 2.85 min, 10-99% CH3CN, 5 min run; ESI-MS m/z 483.5 (M+1)+.

Workup

customThe reaction mixture was partitioned between dichloromethane and water
concentrationThe organic layer was concentrated in vacuo
customthe residue was purified by HPLC (in the absence of TFA)
customto yield the product

Sources & evidence

ORD record: ord-8330b761ce2847acaf83a868525798aa
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08642609B2

Reaction notes

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