Ethanolamine → HCID 10392826, compound

HRID 1181564Notes

Reaction equation

HRID 1181564 reaction equation
[CH3:1][NH:2][C:3]1[N:8]=[C:7]([C:9]2[NH:10][C:11]3[C:16]([CH:17]=2)=[CH:15][C:14]([C:18]([NH:20][CH:21]([CH2:25][N:26]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[C:27]2[N:32]=[CH:31][CH:30]=[CH:29][N:28]=2)[C:22](O)=[O:23])=[O:19])=[CH:13][CH:12]=3)[CH:6]=[CH:5][N:4]=1.C1C=NC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.[CH2:58]([CH2:60][NH2:61])[OH:59]>CN(C=O)C.C(Cl)CCl>[OH:59][CH2:58][CH2:60][NH:61][C:22]([CH:21]([NH:20][C:18]([C:14]1[CH:15]=[C:16]2[C:11](=[CH:12][CH:13]=1)[NH:10][C:9]([C:7]1[CH:6]=[CH:5][N:4]=[C:3]([NH:2][CH3:1])[N:8]=1)=[CH:17]2)=[O:19])[CH2:25][N:26]([C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1)[C:27]1[N:28]=[CH:29][CH:30]=[CH:31][N:32]=1)=[O:23]

Participants

7

Reactant 4

HCID 700EthanolamineHCID 81531DiisopropylethylamineHCID 181649HOAtHCID 58981192HCID 58981192, compound

Product 1

HCID 10392826HCID 10392826, compound

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

200 mg of the acid 48 were dissolved in 2 ml of absolute DMF. 94 mg of HOAt and 158 μl of DIEA were added. 56 μl of ethanolamine were then added dropwise and the mixture was cooled down to 0° C.; 195 mg of EDC were then added. After 2 days of stirring at room temperature, the solvent was evaporated and the crude product was purified by means of MPLC (eluent: DCM:MeOH=9:1).

Workup

  1. customthe solvent was evaporated
  2. customthe crude product was purified by means of MPLC (eluent: DCM:MeOH=9:1)

Sources & evidence

ORD record
ord-9169390c51e7457fbdd5cac859b4225d
Source dataset
uspto-grants-2007_10
Patent number
US07285560B2

Reaction notes

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