Glycolic Acid → HCID 178426064, compound

HRID 1893379Notes

Reaction equation

HRID 1893379 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:56]=[CH:55][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[CH:53]=[C:52]([CH3:54])[O: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:56]=[CH:55][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[CH2:44][CH2:45][C@H:46]([C:49]2[CH:53]=[C:52]([CH3:54])[O:51][N:50]=2)[CH2:47][CH2:48]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 178426061HCID 178426061, compound

Product 1

HCID 178426064HCID 178426064, compoundYield 75%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of glycolic acid (11.9 mg, 0.156 mmol) and HATU (59.4 mg, 0.156 mmol) in N,N-dimethylformamide (1.0 ml) was stirred for 5 minutes at room temperature. trans-8-Chloro-1-[4-(5-methyl-isoxazol-3-yl)-cyclohexyl]-5,6-dihydro-4H-2,3,5,10b-tetraaza-benzo[e]azulene (50.0 mg, 0.130 mmol) and N-ethyldiisopropylamine (0.055 ml, 0.31 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 (43 mg, 75%) as light yellow solid. MS m/e: 442 ([M+H]+).

Sources & evidence

ORD record
ord-1444969cc4a041b29ed3315024da92ee
Source dataset
uspto-grants-2013_08
Patent number
US08513238B2

Reaction notes

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