1-Hydroxybenzotriazole → HCID 89739155, compound

HRID 2278406Notes

Reaction equation

HRID 2278406 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][C:17]([C:20]3[O:24][C:23]([C:25]4[CH:33]=[CH:32][C:31]([C:34]([F:37])([F:36])[F:35])=[C:30]5[C:26]=4[CH:27]=[CH:28][NH:29]5)=[N:22][C:21]=3[C:38](O)=[O:39])=[CH:16][CH:15]=2)[CH2:10][C:9]1([CH3:42])[CH3:41])=[O:7])([CH3:4])([CH3:3])[CH3:2].CC[N:45]=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1>CN(C=O)C.N.O1CCOCC1>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:15]=[CH:16][C:17]([C:20]3[O:24][C:23]([C:25]4[CH:33]=[CH:32][C:31]([C:34]([F:36])([F:35])[F:37])=[C:30]5[C:26]=4[CH:27]=[CH:28][NH:29]5)=[N:22][C:21]=3[C:38](=[O:39])[NH2:45])=[CH:18][CH:19]=2)[CH2:10][C:9]1([CH3:41])[CH3:42])=[O:7])([CH3:3])([CH3:2])[CH3:4]

Participants

7

Reactant 3

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 89739213HCID 89739213, compound

Product 1

HCID 89739155HCID 89739155, compound

Reagents, catalysts & solvents 3

HCID 222AmmoniaSolventHCID 6228DimethylformamideSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of 4-{4-[4-carboxy-2-(7-trifluoromethyl-1H-indol-4-yl)-oxazol-5-yl]-phenyl}-2,2-dimethyl-piperazine-1-carboxylic acid tert-butyl ester, EDCI HCl (0.36 g, 0.002 mol) and HOBt (0.3 g, 0.002 mol) in 15 mL of DMF and 15 mL of NH3 in dioxane was stirred for 2 hrs. The solvents were removed in vacuo. The residue was partitioned between water and EtOAc, the organic phase dried over Na2SO4 and the solvent removed in vacuo to give the crude title compound product (0.18 g crude).

Workup

  1. customThe solvents were removed in vacuo
  2. customThe residue was partitioned between water and EtOAc
  3. dry with materialthe organic phase dried over Na2SO4
  4. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-5ce981ad68cf4a84857e967d27e743e3
Source dataset
uspto-grants-2015_09
Patent number
US09133180B2

Reaction notes

Loading…