N,N-Dimethylglycine → HCID 178483915, compound

HRID 452548Notes

Reaction equation

HRID 452548 reaction equation
[CH3:1][N:2]([CH3:7])[CH2:3][C:4]([OH:6])=[O:5].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[Cl:32][C:33]1[CH:59]=[CH:58][C:36]2[N:37]3[C:41]([CH2:42][NH:43][CH2:44][C:35]=2[CH:34]=1)=[N:40][N:39]=[C:38]3[C@H:45]1[CH2:50][CH2:49][C@H:48]([C:51]2[C:56]([F:57])=[CH:55][CH:54]=[CH:53][N:52]=2)[CH2:47][CH2:46]1.C(N(C(C)C)C(C)C)C>CN(C)C=O.O.CO>[CH:4]([OH:6])=[O:5].[Cl:32][C:33]1[CH:59]=[CH:58][C:36]2[N:37]3[C:41]([CH2:42][N:43]([C:4](=[O:5])[CH2:3][N:2]([CH3:7])[CH3:1])[CH2:44][C:35]=2[CH:34]=1)=[N:40][N:39]=[C:38]3[C@H:45]1[CH2:50][CH2:49][C@H:48]([C:51]2[C:56]([F:57])=[CH:55][CH:54]=[CH:53][N:52]=2)[CH2:47][CH2:46]1

Participants

8

Reactant 4

HCID 673N,N-DimethylglycineHCID 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 178483915HCID 178483915, compoundYield 127.7%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of N,N-dimethylglycine (11.5 mg, 0.151 mmol) and HATU (57.3 mg, 0.151 mmol) in N,N-dimethylformamide (1.0 ml) was stirred for 5 minutes at room temperature. 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 (51 mg, 77%) as white solid. MS m/e: 483 ([M+H]+)

Sources & evidence

ORD record
ord-10a845fbccd847f49c0d1a12b2ad3d19
Source dataset
uspto-grants-2013_07
Patent number
US08492376B2

Reaction notes

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