Ammonia → HCID 57635758, compound

HRID 2109939Notes

Reaction equation

HRID 2109939 reaction equation
[CH3:1][C:2]1[CH:6]=[C:5]([NH:7][C:8]2[N:16]=[CH:15][CH:14]=[CH:13][C:9]=2[C:10](O)=[O:11])[N:4]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[N:3]=1.CC[N:25]=C=NCCCN(C)C.C1C=NC2N(O)N=NC=2C=1.C(N(CC)CC)C.N>ClCCl.CO>[CH3:1][C:2]1[CH:6]=[C:5]([NH:7][C:8]2[N:16]=[CH:15][CH:14]=[CH:13][C:9]=2[C:10]([NH2:25])=[O:11])[N:4]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[N:3]=1

Participants

8

Reactant 5

HCID 222AmmoniaHCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 181649HOAtHCID 57635778HCID 57635778, compound

Product 1

HCID 57635758HCID 57635758, compoundYield 55%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-[(3-methyl-1-phenyl-1H-pyrazol-5-yl)amino]nicotinic acid (40 mg, 0.14 mmol), EDCI (52 mg, 0.27 mmol), HOAT (37 mg, 0.27 mmol), and triethylamine (0.06 mL, 0.41 mmol) in dichloromethane (4 mL) was added ammonia (7 N) in methanol (0.2 mL). The reaction mixture was stirred at rt for 16 h. The organic layer was washed with water, dried over MgSO4, and subsequently concentrated under reduced pressure. The product was purified on a silica gel preparative plate (1000 microns) with EtOAc/hexane (2:1, v/v) to obtain the product as a white solid (22 mg, 55%). 1H NMR (400 MHz, DMSO-d6) δ 2.2 (s, 3H), 6.63 (s, 1H), 6.89 (m, 1H), 7.38 (m, 1H), 7.50 (m, 4H), 7.71 (s, 1H), 8.15 (d, 1H), 8.24 (s, 1H), 8.33 (d, 1H), 11.56 (s, 1H); ES-MS m/z 294.1 (MH+); HPLC RT (min) 2.02.

Workup

  1. washThe organic layer was washed with water
  2. dry with materialdried over MgSO4
  3. concentrationsubsequently concentrated under reduced pressure
  4. customThe product was purified on a silica gel preparative plate (1000 microns) with EtOAc/hexane (2:1

Sources & evidence

ORD record
ord-514dbe286b5a4fb183d39923192927c3
Source dataset
uspto-grants-2009_04
Patent number
US07517878B2

Reaction notes

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