N,N-Dimethylglycine → HCID 178426063, compound

HRID 1893380Notes

Reaction equation

HRID 1893380 reaction equation
[CH3:1][N:2]([CH3:7])[CH2:3][C:4](O)=[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:58]=[CH:57][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[CH:55]=[C:54]([CH3:56])[O:53][N:52]=2)[CH2:47][CH2:46]1.C(N(C(C)C)C(C)C)C>CN(C)C=O.O.CO>[Cl:32][C:33]1[CH:58]=[CH:57][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[CH2:46][CH2:47][C@H:48]([C:51]2[CH:55]=[C:54]([CH3:56])[O:53][N:52]=2)[CH2:49][CH2:50]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 178426061HCID 178426061, compound

Product 1

HCID 178426063HCID 178426063, compoundYield 83.7%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of N,N-dimethylglycine (16.1 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-ethyl diisopropylamine (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 (51 mg, 76%) as off-white solid. MS m/e: 469 ([M+H]+).

Sources & evidence

ORD record
ord-d0015045a32c40ad9ba5537b88a8308b
Source dataset
uspto-grants-2013_08
Patent number
US08513238B2

Reaction notes

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