Glycolic Acid → HCID 178521481, compound

HRID 452547Notes

Reaction equation

HRID 452547 reaction equation
[C:1]([OH:5])(=O)[CH2:2][OH:3].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[Cl:30][C:31]1[CH:57]=[CH:56][C:34]2[N:35]3[C:39]([CH2:40][NH:41][CH2:42][C:33]=2[CH:32]=1)=[N:38][N:37]=[C:36]3[C@H:43]1[CH2:48][CH2:47][C@H:46]([C:49]2[C:54]([F:55])=[CH:53][CH:52]=[CH:51][N:50]=2)[CH2:45][CH2:44]1.C(N(C(C)C)C(C)C)C>CN(C)C=O.O.CO>[Cl:30][C:31]1[CH:57]=[CH:56][C:34]2[N:35]3[C:39]([CH2:40][N:41]([C:1](=[O:5])[CH2:2][OH:3])[CH2:42][C:33]=2[CH:32]=1)=[N:38][N:37]=[C:36]3[C@H:43]1[CH2:48][CH2:47][C@H:46]([C:49]2[C:54]([F:55])=[CH:53][CH:52]=[CH:51][N:50]=2)[CH2:45][CH2:44]1

Participants

8

Reactant 4

HCID 757Glycolic AcidHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 178505857HCID 178505857, compound

Product 1

HCID 178521481HCID 178521481, compoundYield 71.4%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of glycolic acid (11.5 mg, 0.151 mmol) and HATU (57.3 mg, 0.151 mmol) in N,N-dimethylformamide (1.0 ml) was stirred at room temperature for 5 minutes. trans-8-Chloro-1-[4-(3-fluoro-pyridin-2-yl)-cyclohexyl]-5,6-dihydro-4H-2,3,5,10b-tetraaza-benzo[e]azulene (50.0 mg, 0.126 mmol) and N-ethyldiisopropylamine (0.053 ml, 0.30 mmol) were added consecutively. The reaction mixture was stirred for 1 h. Preparative RP-HPLC with water (0.05% formic acid)/methanol as eluent gave the title compound (41 mg, 71%) as white solid. MS m/e: 456 ([M+H]+)

Sources & evidence

ORD record
ord-a3e9b5a679c84697a47d7adb672af115
Source dataset
uspto-grants-2013_07
Patent number
US08492376B2

Reaction notes

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