N,N-Dimethylglycine → HCID 10412210, compound

HRID 1243587Notes

Reaction equation

HRID 1243587 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-d2e7c397bd374516a3fae32572939a4c
Source dataset
uspto-grants-2006_10
Patent number
US07119088B2

Reaction notes

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