N,N-Dimethylglycine → HCID 10412210, compound

HRID 2118041Notes

Reaction equation

HRID 2118041 reaction equation
CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[Cl:25][C:26]1[CH:51]=[CH:50][C:29]2[N:30]3[C:34]([CH2:35][NH:36][CH2:37][C:28]=2[CH:27]=1)=[N:33][N:32]=[C:31]3[CH:38]1[CH2:43][CH2:42][N:41]([C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][N:45]=2)[CH2:40][CH2:39]1.C(N(CC)CC)C.[CH3:59][N:60]([CH2:62][C:63](O)=[O:64])[CH3:61]>CN(C)C(=O)C>[Cl:25][C:26]1[CH:51]=[CH:50][C:29]2[N:30]3[C:34]([CH2:35][N:36]([C:63](=[O:64])[CH2:62][N:60]([CH3:61])[CH3:59])[CH2:37][C:28]=2[CH:27]=1)=[N:33][N:32]=[C:31]3[CH:38]1[CH2:39][CH2:40][N:41]([C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][N:45]=2)[CH2:42][CH2:43]1

Participants

6

Reactant 4

HCID 673N,N-DimethylglycineHCID 8471TriethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 113264888-Chloro-1-(3,4,5,6-tetrahydro-2h-[1,2']bipyridinyl-4-yl)-5,6-dihydro4h-2,3,5,10b-tetraaza-benzo[e]azulene

Product 1

HCID 10412210HCID 10412210, compoundYield 57.8%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent2×

Conditions

Temperature
50 °C

Procedure

A solution of HBTU (152 mg, 0.38 mmol) in N,N-dimethylacetamide (1.9 ml) was added to a solution of the amine of example 4 (97 mg, 0.26 mmol), triethylamine (1.5 μl, cat.) and dimethylamino-acetic acid (36 mg, 0.26 mmol) in N,N-dimethylacetamide (2.5 ml) and heated to 50° C. for 2 hours. The mixture was cooled and the solvent evaporated under reduced pressure. The residue was partitioned between dichloromethane (10 ml) and 2M aqueous sodium hydroxide solution (10 ml). The organic phase was dried over magnesium sulphate before being evaporated under reduced pressure and purified by chromatography on silica gel using methanol and ammonium hydroxide in dichloromethane (7:1:93) as eluant to afford the title compound (70 mg) as a brown foam.

Workup

  1. temperatureThe mixture was cooled
  2. customthe solvent evaporated under reduced pressure
  3. customThe residue was partitioned between dichloromethane (10 ml) and 2M aqueous sodium hydroxide solution (10 ml)
  4. dry with materialThe organic phase was dried over magnesium sulphate
  5. custombefore being evaporated under reduced pressure
  6. custompurified by chromatography on silica gel

Sources & evidence

ORD record
ord-aba9146165df47409edd324aff5f85fd
Source dataset
uspto-grants-2008_10
Patent number
US07442795B2

Reaction notes

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