Hydrochloric Acid → HCID 178457702, compound

HRID 526508Notes

Reaction equation

HRID 526508 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:10]=[N:11][N:12]([C:15]3[CH:23]=[CH:22][C:18]([C:19](O)=[O:20])=[CH:17][N:16]=3)[C:13]=2[OH:14])=[CH:5][CH:4]=1)#[N:2].CCN=C=NCCCN(C)C.C1[CH:40]=[C:39]2[N:41]=NN(O)[C:38]2=CC=1.O.CCN(C(C)C)C(C)C.CC(N)C.Cl>CN(C=O)C.O>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([C:9]2[CH:10]=[N:11][N:12]([C:15]3[CH:23]=[CH:22][C:18]([C:19]([NH:41][CH:39]([CH3:40])[CH3:38])=[O:20])=[CH:17][N:16]=3)[C:13]=2[OH:14])=[CH:7][CH:8]=1)#[N:2]

Participants

9

Reactant 6

HCID 313Hydrochloric AcidHCID 6363IsopropylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 81531DiisopropylethylamineHCID 27960291-Hydroxybenzotriazole hydrateHCID 178509615HCID 178509615, compound

Product 1

HCID 178457702HCID 178457702, compoundYield 54.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Combined 6-(4-(4-cyanophenyl)-5-hydroxy-1H-pyrazol-1-yl)nicotinic acid (100 mg, 0.327 mmol), EDCI (94 mg, 0.490 mmol), HOBT hydrate (75 mg, 0.490 mmol) in DMF (1 mL) and then add Hunig's base (127 mg, 0.980 mmol). Then propan-2-amine (28.9 mg, 0.490 mmol) was added and the mixture was stirred at ambient temperature for 16 h. The mixture was diluted with water (4 mL) and acidified with 1N HCl to pH=5-6 to give a solid. The solid was collected by filtration, washed with water (2 mL), and recrystallized from hot MeOH (3-6 mL) to give the title compound (62.0 mg, 54.7% yield) as an off-white solid. MS m/z [M+H]+ 348.

Workup

  1. customto give a solid
  2. filtrationThe solid was collected by filtration
  3. washwashed with water (2 mL)
  4. customrecrystallized from hot MeOH (3-6 mL)

Sources & evidence

ORD record
ord-710ecee8678c45cd9977e557331f8dc5
Source dataset
uspto-grants-2016_05
Patent number
US09345713B2

Reaction notes

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