4-Methoxybenzylamine → HCID 59174316, compound

HRID 1481665Notes

Reaction equation

HRID 1481665 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-e0bc76dfcb394c6f9e74accc526f2292
Source dataset
uspto-grants-2016_08
Patent number
US09409921B2

Reaction notes

Loading…