1-Hydroxybenzotriazole → HCID 55556362, compound

HRID 392774Notes

Reaction equation

HRID 392774 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11]([OH:13])=O)=[CH:5]2.[N:14]1([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl>CN(C)C1C=CN=CC=1.C(Cl)Cl>[C:23]([O:22][C:20]([N:14]1[CH2:19][CH2:18][N:17]([C:11]([C:6]2[NH:7][C:8]3[C:4]([CH:5]=2)=[CH:3][C:2]([Cl:1])=[CH:10][CH:9]=3)=[O:13])[CH2:16][CH2:15]1)=[O:21])([CH3:26])([CH3:24])[CH3:25]

Participants

7

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 826935-Chloro-1H-indole-2-carboxylic acidHCID 143452tert-Butyl piperazine-1-carboxylateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 55556362HCID 55556362, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 5-chloroindole-2-carboxylic acid (10 g), tert-butyl 1-piperazinecarboxylate (10.5 g) and 4-dimethylaminopyridine (6.3 g) in CH2Cl2 (200 mL) was treated with a catalytic amount of HOBT (0.2 g). The resulting mixture was cooled to 0° C., and EDCl (10.8 g) was added. The reaction was then slowly warmed to ambient temperature and stirred for 24 h then concentrated under reduced pressure. Water was added to the resulting residue. The product precipitated and was washed with water (2×50 mL) and Et2O (30 mL). The resulting solid was dried under reduced pressure to yield (18.2 g). MS (electrospray): exact mass calculated for C18H22ClN3O3, 363.13; m/z found, 362.3 [M−H]−.

Workup

  1. temperatureThe reaction was then slowly warmed to ambient temperature
  2. concentrationthen concentrated under reduced pressure
  3. additionWater was added to the resulting residue
  4. customThe product precipitated
  5. washwas washed with water (2×50 mL) and Et2O (30 mL)
  6. customThe resulting solid was dried under reduced pressure
  7. customto yield (18.2 g)

Sources & evidence

ORD record
ord-53a8ec08d7e64fd1990aaa072f70986a
Source dataset
uspto-grants-2004_10
Patent number
US06803362B2

Reaction notes

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