1-Hydroxybenzotriazole hydrate → HCID 9811366, compound

HRID 1978510Notes

Reaction equation

HRID 1978510 reaction equation
[N:1]1[CH:2]=[C:3]2[N:12]3[C:7](=[CH:8][CH:9]=[CH:10][C:11]=13)[S:6][C:5]([C:13]([OH:15])=O)=[CH:4]2.Cl.Cl.[NH2:18][CH:19]1[CH2:24][CH2:23][N:22]([CH2:25][CH2:26][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH2:21][CH2:20]1.O.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(CC)CC)C>CN(C)C=O.C(N(CC)CC)C>[C:28]1([CH2:27][CH2:26][CH2:25][N:22]2[CH2:23][CH2:24][CH:19]([NH:18][C:13]([C:5]3[S:6][C:7]4[N:12]5[C:3](=[CH:2][N:1]=[C:11]5[CH:10]=[CH:9][CH:8]=4)[CH:4]=3)=[O:15])[CH2:20][CH2:21]2)[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1

Participants

7

Reactant 4

HCID 27960291-Hydroxybenzotriazole hydrateHCID 99645121-(3-Diethylaminopropyl)-3-ethylcarbodiimide hydrochlorideHCID 10943925HCID 10943925, compoundHCID 219940191-(3-Phenylpropyl)piperidin-4-amine--hydrogen chloride (1/2)

Product 1

HCID 9811366HCID 9811366, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
50 °C

Procedure

A suspension of 5-thia-1,8b-diazaacenaphthylene-4-carboxylic acid (1.2 g), 4-amino-1-(3-phenylpropan-1-yl)piperidine dihydrochloride (1.5 g), triethylamine (1.5 ml), 1-hydroxy-1H-benzotriazole monohydrate (0.8 g), and 1-ethyl-3-(3-diethylaminopropyl)carbodiimide hydrochloride (1.0 g) in N,N-dimethylformamide (15 ml) was stirred at 50° C. for 2 hours. After spontaneous cooling, this reaction mixture was extracted with ethyl acetate/tetrahydrofuran (4/1; 90 ml). The organic layer was washed with 1N-aqueous solution of sodium hydroxide (10 ml) and water (30 ml) and concentrated. The resulting crystal crop was rinsed with diisopropyl ether (20 ml) and dried to provide the title compound (2.0 g, 95%).

Workup

  1. extractionAfter spontaneous cooling, this reaction mixture was extracted with ethyl acetate/tetrahydrofuran (4/1; 90 ml)
  2. washThe organic layer was washed with 1N-aqueous solution of sodium hydroxide (10 ml) and water (30 ml)
  3. concentrationconcentrated
  4. washThe resulting crystal crop was rinsed with diisopropyl ether (20 ml)
  5. customdried

Sources & evidence

ORD record
ord-91fa1adc0e544fe38bc8d3099e9b6ae0
Source dataset
uspto-grants-2001_05
Patent number
US06235731B1

Reaction notes

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