Dimethylformamide → HCID 68590505, compound

HRID 1429167Notes

Reaction equation

HRID 1429167 reaction equation
[CH2:1]([O:3][C:4]([C:6]1([NH:11][C:12]([CH:14]2[CH2:18][CH:17]([O:19][C:20]3[CH:25]=[C:24]([C:26]4[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][CH:27]=4)[N:23]=[C:22]([O:34][CH3:35])[N:21]=3)[CH2:16][CH:15]2C(O)=O)=[O:13])[CH2:8][CH:7]1[CH:9]=[CH2:10])=[O:5])[CH3:2].CN[CH:41]=[CH:42][CH2:43][CH2:44][CH2:45]C.CCN(C(C)C)C(C)C.[CH3:56][N:57]([CH:59]=[O:60])[CH3:58]>>[CH2:1]([O:3][C:4]([C:6]1([NH:11][C:12]([CH:14]2[CH2:18][CH:17]([O:19][C:20]3[CH:25]=[C:24]([C:26]4[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][CH:27]=4)[N:23]=[C:22]([O:34][CH3:35])[N:21]=3)[CH2:16][CH:15]2[C:59](=[O:60])[N:57]([CH2:58][CH2:45][CH2:44][CH2:43][CH:42]=[CH2:41])[CH3:56])=[O:13])[CH2:8][CH:7]1[CH:9]=[CH2:10])=[O:5])[CH3:2]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 81531DiisopropylethylamineHCID 68590308HCID 68590308, compoundHCID 86641378HCID 86641378, compound

Product 1

HCID 68590505HCID 68590505, compoundYield 82%

Procedure

The acid 16c (1.2 g, 2 mmol) was reacted with N-methylhexeneamine (340 mg, 3.0 mmol) and DIEA (1.29 g, 10.0 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, (1.02 g, 82%), (M+H)+621.

Workup

  1. customPurification by column chromatography on silica gel

Sources & evidence

ORD record
ord-09ff335a3afd41f095305fb521cbc2bf
Source dataset
uspto-grants-2015_01
Patent number
US08937080B2

Reaction notes

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