Diisopropylethylamine → HCID 68590844, compound

HRID 1429180Notes

Reaction equation

HRID 1429180 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[C:7]([O:9][CH:10]2[CH2:14][CH:13]([C:15](O)=[O:16])[CH:12]([C:18](=[O:30])[NH:19][C:20]3([C:25]([O:27][CH2:28][CH3:29])=[O:26])[CH2:22][CH:21]3[CH:23]=[CH2:24])[CH2:11]2)[CH:6]=[C:5]([O:31][CH3:32])[N:4]=1.[CH3:33][NH:34][CH:35]=[CH:36][CH2:37][CH2:38][CH2:39][CH3:40].CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[CH2:28]([O:27][C:25]([C:20]1([NH:19][C:18]([CH:12]2[CH2:11][CH:10]([O:9][C:7]3[CH:6]=[C:5]([O:31][CH3:32])[N:4]=[C:3]([O:2][CH3:1])[N:8]=3)[CH2:14][CH:13]2[C:15](=[O:16])[N:34]([CH2:35][CH2:36][CH2:37][CH2:38][CH:39]=[CH2:40])[CH3:33])=[O:30])[CH2:22][CH:21]1[CH:23]=[CH2:24])=[O:26])[CH3:29]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 68590687HCID 68590687, compoundHCID 86641378HCID 86641378, compound

Product 1

HCID 68590844HCID 68590844, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The acid 18d (1.2 g, 2 mmol) was reacted with N-methylhexeneamine (0.34 g, 3.0 mmol), DIEA (1.29 g, 10.0 mmol) and HATU (1.1 g, 3 mmol) in dry DMF (30 ml) according to the procedure described in Example 13 step c. Purification by column chromatography on silica gel gave the title compound (0.74 g, 74%), (M+H)+545.

Workup

  1. customPurification by column chromatography on silica gel

Sources & evidence

ORD record
ord-369205f2dfb34f168a59165c5b2a07c2
Source dataset
uspto-grants-2015_01
Patent number
US08937080B2

Reaction notes

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