Diisopropylethylamine → HCID 178523366, compound

HRID 1480432Notes

Reaction equation

HRID 1480432 reaction equation
[NH:1]1[CH:5]=[C:4]([C:6]([OH:8])=O)[N:3]=[N:2]1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.[NH2:42][CH2:43][CH2:44][CH2:45][N:46]1[CH2:51][CH2:50][N:49]([C:52]([O:54][CH2:55][C:56]2[CH:61]=[C:60]([Cl:62])[CH:59]=[C:58]([Cl:63])[CH:57]=2)=[O:53])[CH2:48][CH2:47]1>CN(C=O)C.CCOC(C)=O>[NH:1]1[CH:5]=[C:4]([C:6]([NH:42][CH2:43][CH2:44][CH2:45][N:46]2[CH2:51][CH2:50][N:49]([C:52]([O:54][CH2:55][C:56]3[CH:61]=[C:60]([Cl:62])[CH:59]=[C:58]([Cl:63])[CH:57]=3)=[O:53])[CH2:48][CH2:47]2)=[O:8])[N:3]=[N:2]1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 1401204-Carboxy-1,2,3-triazoleHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 90218727HCID 90218727, compound

Product 1

HCID 178523366HCID 178523366, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To 1H-1,2,3-triazole-4-carboxylic acid (32.7 mg, 0.289 mmol) in DMF (2 ml) was added HATU (110 mg, 0.289 mmol) and DIPEA (0.050 ml, 0.289 mmol). The resulting yellow solution was stirred for 10 mins and treated with 3,5-dichlorobenzyl 4-(3-amino propyl)piperazine-1-carboxylate (step 2) (100 mg, 0.289 mmol). After stirring at ambient temperature for 4 hrs, the mixture was diluted with EtOAc (50 ml) and washed with water (2×10 ml). The organic extracts were dried (MgSO4) and concentrated under reduced pressure. The residue was dissolved in DCM and applied to a 20 g silica cartridge eluting with 10% MeOH/DCM containing 1% aqueous 880 ammonia. The product fractions were concentrated to give 3,5-dichlorobenzyl 4-(3-(1H-1,2,3-triazole-4-carboxamido)propyl)piperazine-1-carboxylate as a white foam;

Workup

  1. stirringAfter stirring at ambient temperature for 4 hrs
  2. washwashed with water (2×10 ml)
  3. dry with materialThe organic extracts were dried (MgSO4)
  4. concentrationconcentrated under reduced pressure
  5. dissolutionThe residue was dissolved in DCM
  6. washeluting with 10% MeOH/DCM containing 1% aqueous 880 ammonia
  7. concentrationThe product fractions were concentrated

Sources & evidence

ORD record
ord-507038a1cfe645e09c13cb235e05cf51
Source dataset
uspto-grants-2016_08
Patent number
US09409895B2

Reaction notes

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