2-Aminopropanol → HCID 58025758, compound

HRID 1046952Notes

Reaction equation

HRID 1046952 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:12][CH:11]([C:13]3[C:14]([O:24][CH3:25])=[C:15]([CH:21]=[CH:22][CH:23]=3)[O:16][CH2:17][C:18](O)=[O:19])[N:10]([C:26](=[O:34])[C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=3[OH:33])[N:9]=2)=[CH:4][CH:3]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.[NH2:68][CH:69]([CH3:72])[CH2:70][OH:71]>CN(C=O)C.CCO>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:12][CH:11]([C:13]3[C:14]([O:24][CH3:25])=[C:15]([CH:21]=[CH:22][CH:23]=3)[O:16][CH2:17][C:18]([NH:68][CH:69]([CH3:72])[CH2:70][OH:71])=[O:19])[N:10]([C:26](=[O:34])[C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=3[OH:33])[N:9]=2)=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 51262-AminopropanolHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 67279451HCID 67279451, compound

Product 1

HCID 58025758HCID 58025758, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6228DimethylformamideSolvent

Procedure

To {3-[5-(4-Fluoro-phenyl)-3-(2-hydroxy-benzoyl)-2,3-dihydro-[1,3,4]thiadiazol-2-yl]-2-methoxy-phenoxy}-acetic acid (0.27 mmol) in dry DMF (0.5 mL) is added HATU (1.35 mmol), DIEA (0.45 mL, 2.7 mmol) and 2-amino-propan-1-ol. The mixture is kept at ambient temperature for 16 hours. The residue is diluted with EtOH (1 mL). Purification of the mixture by preparative LC/MS (30-100% MeCN/H2O) gives 2-{3-[5-(4-fluoro-phenyl)-3-(2-hydroxy-benzoyl)-2,3-dihydro-[1,3,4]thiadiazol-2-yl]-2-methoxy-phenoxy}-N-(2-hydroxy-1-methyl-ethyl)-acetamide. 1H NMR (400 MHz, CDCl3) δ 11.2 (s, 1H), 8.53 (m, 1H), 7.73 (m, 2H), 7.6 (s, 1H), 7.44 (t, J=8.4 Hz, 1H), 7.15 (t, J=8 Hz, 2H), 6.9-7.1 (m, 5H), 4.58 (s, 2H), 4.14 (m, 1H), 4.06 (s, 3H), 3.69 (m, 1H), 3.59 (m, 1H), 2.1 (bs, 2H), 1.23 (m, 3H); LC/MS (ES+): 540.1 (M+1)+.

Workup

  1. customPurification of the mixture by preparative LC/MS (30-100% MeCN/H2O)

Sources & evidence

ORD record
ord-91a1d964b4464013811f8afff5f6e7ba
Source dataset
uspto-grants-2013_10
Patent number
US08569345B2

Reaction notes

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