Ethylamine hydrochloride → HCID 16222413, compound

HRID 237346Notes

Reaction equation

HRID 237346 reaction equation
[CH3:1][CH2:2][N:3](C(C)C)C(C)C.[CH:10]1[C:23]2[NH:22][C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[S:15][C:14]=2[CH:13]=[CH:12][C:11]=1[C:24]([OH:26])=O.Cl.C(N)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C([O-])(O)=O.[Na+]>CN(C=O)C.CCOCC.CCOC(C)=O>[CH2:2]([NH:3][C:24]([C:11]1[CH:12]=[CH:13][C:14]2[S:15][C:16]3[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=3)[NH:22][C:23]=2[CH:10]=1)=[O:26])[CH3:1]

Participants

9

Reactant 5

HCID 11198Ethylamine hydrochlorideHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 2271159310H-Phenothiazine-2-carboxylic acid

Product 1

HCID 16222413HCID 16222413, compound

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

5.8 ml (3.3 eq.) of DIEA is added dropwise to a solution of 2.43 g (10 mmoles) of 10H-phenothiazine-2-carboxylic acid, 1.79 g (2.2 eq.) of ethylamine hydrochloride and 4.17 g (1.1 eq.) of HBTU in 50 ml of DMF, cooled down to 0° C. The reaction mixture is stirred for 15 hours at 23° C., and then poured into a mixture of 100 ml of a saturated solution of NaHCO3 and 100 ml of AcOEt. After stirring for a few minutes, the precipitate formed is removed by filtration and the filtrate is decanted. The organic phase is successively washed with water, a 1M solution of citric acid and salt water. The organic solution is dried over sodium sulphate, filtered and concentrated to dryness under vacuum. The solid obtained is suspended in Et2O, triturated and filtered. A beige solid is obtained with a quantitative yield. Melting point: 150-151° C.

Workup

  1. stirringAfter stirring for a few minutes
  2. customthe precipitate formed
  3. customis removed by filtration
  4. customthe filtrate is decanted
  5. washThe organic phase is successively washed with water
  6. dry with materialThe organic solution is dried over sodium sulphate
  7. filtrationfiltered
  8. concentrationconcentrated to dryness under vacuum
  9. customThe solid obtained
  10. customtriturated
  11. filtrationfiltered
  12. customA beige solid is obtained with a quantitative yield

Sources & evidence

ORD record
ord-676ec24f2d3d4176bda46d1aed4ebd4b
Source dataset
uspto-grants-2014_02
Patent number
US08642591B2

Reaction notes

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