Ammonia → HCID 24829351, compound

HRID 1712962Notes

Reaction equation

HRID 1712962 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]1[N:12]([C:13]([C:15]2[S:19][C:18]([C:20]3[CH:21]=[C:22]([CH:25]=[CH:26][CH:27]=3)[C:23]#[N:24])=[CH:17][CH:16]=2)=[O:14])[N:11]=[C:10]([C:28]2[CH:29]=[N:30][CH:31]=[CH:32][CH:33]=2)[CH2:9]1.N>CO.[Ni]>[NH2:24][CH2:23][C:22]1[CH:21]=[C:20]([C:18]2[S:19][C:15]([C:13]([N:12]3[CH:8]([C:3]4[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=4[OH:1])[CH2:9][C:10]([C:28]4[CH:29]=[N:30][CH:31]=[CH:32][CH:33]=4)=[N:11]3)=[O:14])=[CH:16][CH:17]=2)[CH:27]=[CH:26][CH:25]=1

Participants

5

Reactant 2

HCID 222AmmoniaHCID 24968215HCID 24968215, compound

Product 1

HCID 24829351HCID 24829351, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

To a solution of 3-(5-{[5-(2-hydroxyphenyl)-3-pyridin-3-yl-4,5-dihydro-1H-pyrazol-1-yl]carbonyl}-2-thienyl)benzonitrile in 7M mixture of ammonia in MeOH was added Raney nickel (3 mL). The reaction mixture was allowed to stir at rt under an atmosphere of hydrogen for 2 days. The resulting solution was filtered over a pad of celite and the filtrate was concentrated. The crude product was purified via HPLC to give 2-[1-({5-[3-(aminomethyl)phenyl]-2-thienyl}carbonyl)-3-pyridin-3-yl-4,5-dihydro-1H-pyrazol-5-yl]phenol (I-2) (0.073 g, 0.138 mmol) as a white solid. LCMS: (FA) ES+ 455.4, ES-453.4. 1H NMR (400 MHz, d6-DMSO) δ: 9.05-9.08 (m, 1H), 8.66-8.70 (m, 1H), 8.35 (s, 1H), 8.26-8.31 (m, 1H), 8.05 (d, 1H), 7.78-7.82 (m, 1H), 7.64-7.68 (m, 1H), 7.53-7.59 (m, 2H), 7.36-7.47 (m, 2H), 7.08 (t, 1H), 6.92-6.97 (m, 1H), 6.81-6.86 (m, 1H), 6.72 (t, 1H), 5.85 (dd, 1H), 3.89-3.95 (m, 1H), 3.88 (s, 2H), and 3.16-3.24 (m, 1H).

Workup

  1. filtrationThe resulting solution was filtered over a pad of celite
  2. concentrationthe filtrate was concentrated
  3. customThe crude product was purified via HPLC

Sources & evidence

ORD record
ord-389734316e8b4bef9577497ae6924fae
Source dataset
uspto-grants-2010_09
Patent number
US07795249B2

Reaction notes

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