Methanol → HCID 57572491, compound

HRID 1038290Notes

Reaction equation

HRID 1038290 reaction equation
[CH2:1]([O:8][C:9]1[C:21]([C:22]([N:24]2[CH2:28][CH2:27][S:26][C:25]2=[S:29])=[O:23])=[CH:20][C:12]([C:13]([NH:15][CH2:16][CH2:17][O:18][CH3:19])=[O:14])=[CH:11][C:10]=1[C:30]([N:32]1CCS[C:33]1=S)=[O:31])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CN.CO>ClCCl>[CH2:1]([O:8][C:9]1[C:21]([C:22]([N:24]2[CH2:28][CH2:27][S:26][C:25]2=[S:29])=[O:23])=[CH:20][C:12]([C:13]([NH:15][CH2:16][CH2:17][O:18][CH3:19])=[O:14])=[CH:11][C:10]=1[C:30]([NH:32][CH3:33])=[O:31])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 6329MethylamineHCID 57572485HCID 57572485, compound

Product 1

HCID 57572491HCID 57572491, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of compound 18A (2.1 g, 3.65 mmol) in dichloromethane (100 mL), a solution of 0.1 mL methylamine solution (40% wt in water, d=0.902) and 50 mL dichloromethane was added dropwise over 24 h. The reaction progress was monitored by TLC chromatography. When the reaction was judged complete, the reaction mixture was directly applied to a gradient flash silica column (1-5% methanol in dicholoromethane). The desired product was obtained as yellow, thick oil; yield 1.22 g, (69% based on compound 18A).

Sources & evidence

ORD record
ord-7296517b5fb0417ab83a0c4be1523f6e
Source dataset
uspto-grants-2013_10
Patent number
US08551453B2

Reaction notes

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