4-Methoxybenzylamine → HCID 59174316, compound

HRID 2097371Notes

Reaction equation

HRID 2097371 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:10]=[C:11]([CH:24]=[CH:25][CH:26]=1)[O:12][C:13]1[C:18]([C:19]([OH:21])=O)=[CH:17][N:16]=[C:15]([S:22][CH3:23])[N:14]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].COC1C=CC(CN)=CC=1.CN(C(O[N:45]1N=N[C:47]2[CH:48]=[CH:49][CH:50]=[CH:51][C:46]1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CCN(C(C)C)C(C)C>CC#N.CCOC(C)=O.CCCCCC>[C:1]([O:5][C:6](=[O:7])[NH:8][C:9]1[CH:26]=[CH:25][CH:24]=[C:11]([O:12][C:13]2[C:18]([C:19](=[O:21])[NH:45][C:46]3[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=3)=[CH:17][N:16]=[C:15]([S:22][CH3:23])[N:14]=2)[CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 754524-MethoxybenzylamineHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 59174529HCID 59174529, compound

Product 1

HCID 59174316HCID 59174316, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

Acid 4 was directly mixed with 4-methoxybenzylamine (1.55 g, 11.3 mmol), TBTU (5.4 g, 16.8 mmol) and DIEA (2.4 mL, 13.4 mmol) in 100 mL MeCN at room temperature. The reaction mixture was run overnight to give 6 as a white solid (4.2 g, 8.5 mmol) after flash chromatography (EtOAc-hexane).

Sources & evidence

ORD record
ord-053dd6fc70734e2390853d8ffa4456d7
Source dataset
uspto-grants-2013_05
Patent number
US08450335B2

Reaction notes

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