Methanol → HCID 10150405, compound

HRID 1581474Notes

Reaction equation

[CH3:1][O:2][C:3]1[C:11]2[CH:10]=[C:9]([NH2:12])[S:8][C:7]=2[C:6]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:5][CH:4]=1.C(N(CC)C(C)C)C.Cl.[CH3:28][C:29]1[CH:36]=[CH:35][C:32]([CH2:33]Cl)=[CH:31][N:30]=1.C[OH:38]>C1COCC1.ClCCl>[CH3:1][O:2][C:3]1[C:11]2[CH:10]=[C:9]([NH:12][C:33](=[O:38])[C:32]3[CH:35]=[CH:36][C:29]([CH3:28])=[N:30][CH:31]=3)[S:8][C:7]=2[C:6]([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)=[CH:5][CH:4]=1

Participants

Conditions

Temperature: 20 °C

Procedure

A solution of (4-methoxy-7-phenyl-benzo[b]thiophen-2-yl)-amine (100 mg, 0.392 mmol) in THF (8 ml) and diethylisopropyl amine (0.147 ml, 2.2 eq.) was stirred together at −10° C. under an argon atmosphere. To this was slowly added 6-methyl-nicotinyl chloride hydrochloride (83 mg, 0.431 mmol, 1.1 eq) in dichloromethane (5 ml) and the mixture stirred to 20° C. overnight. The reaction was again cooled to 0° C. and Methanol was then added (1.2 ml) and the mixture stirred for 30 min to 20° C. The mixture was then evaporated to dryness and chromatographed over silica gel eluting with a gradient of heptane/EtOAc (1:1 to 1:8). The product fractions were pooled and evaporated to afford the title compound (83 mg, 57% yield) as a yellow solid MS: m/e=375.4 (M+H+).

Workup

temperatureThe reaction was again cooled to 0° C.
stirringthe mixture stirred for 30 min to 20° C
customThe mixture was then evaporated to dryness
customchromatographed over silica gel eluting with a gradient of heptane/EtOAc (1:1 to 1:8)
customevaporated

Sources & evidence

ORD record: ord-81a3aa19ba794b3bbfec89baba33aca6
Source dataset: uspto-grants-2004_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06730670B2

Reaction notes

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