Hydrochloric Acid → HCID 178461435, compound

HRID 526510Notes

Reaction equation

HRID 526510 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]([OH:21])=O)=[CH:17][N:16]=3)[C:13]=2[OH:14])=[CH:5][CH:4]=1)#[N:2].CCN=C=NCCCN(C)C.[CH:35]1[CH:40]=[C:39]2N=N[N:43](O)[C:38]2=CC=1.O.CCN(C(C)C)C(C)C.C[C@H]1C[C@@H]1N.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:43][C@H:38]4[CH2:39][C@@H:40]4[CH3:35])=[O:21])=[CH:17][N:16]=3)[C:13]=2[OH:14])=[CH:7][CH:8]=1)#[N:2]

Participants

9

Reactant 6

HCID 313Hydrochloric AcidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 81531DiisopropylethylamineHCID 27960291-Hydroxybenzotriazole hydrateHCID 51723334HCID 51723334, compoundHCID 178509615HCID 178509615, compound

Product 1

HCID 178461435HCID 178461435, compoundYield 67.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

Combine 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 added Hunig's base (127 mg, 0.980 mmol). Then (1s,2s)-2-methylcyclopropanamine (34.8, 0.490 mmol) was added and the mixture was stirred at 60° C. for 3 h. The reaction 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 (79.2 mg, 67.5% yield) as a white solid. MS m/z [M+H]+ 360.

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-ce9b09b7dcba4019aaf5b0ad383617ee
Source dataset
uspto-grants-2016_05
Patent number
US09345713B2

Reaction notes

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