Water → HCID 67334059, compound

HRID 1673196Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[CH:8][CH:7]=[C:6]2[CH:13]1[CH2:15][O:14]1.[C:16]([O-:19])([O-])=[O:17].[K+].[K+].[OH2:22].[NH4+:23].[OH-].[CH3:25][C:26](=O)[O:27][CH2:28][CH3:29]>CN(C=O)C.CC(=O)OCC.CO>[O:27]1[C:26]2[CH:25]=[CH:4][C:3]([N:23]3[CH2:13][C:6]4([CH2:7][CH2:8][N:9]([CH2:15][CH:13]([OH:14])[C:6]5[C:5]6[C:10](=[CH:11][CH:12]=[C:3]([O:2][CH3:1])[CH:4]=6)[N:9]=[CH:8][CH:7]=5)[CH2:10][CH2:5]4)[O:19][C:16]3=[O:17])=[CH:12][C:11]=2[O:22][CH2:29][CH2:28]1

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of intermediate 4.iii (0.12 g, 0.4 mmol), 6-methoxy-4-oxiranyl-quinoline (0.083 g, 0.4 mmol, prepared according to WO 00/78748), K2CO3 (0.08 g, 0.58 mmol) and LiClO4 (0.048 g, 0.46 mmol) in DMF (4 ml) was heated at 90° C. overnight. The mixture was poured into water and diluted with EA. The yield after work up and chromatography (EA:MeOH 9:1 containing 1% NH4OH) was 0.065 g (32% yield; beige foam).

Workup

customThe yield after work up

Sources & evidence

ORD record: ord-a237cf4f90d944cfb64aa08463aef1e6
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07999115B2

Reaction notes

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