Triethylamine → HCID 58102836, compound

HRID 384981Notes

Reaction equation

HRID 384981 reaction equation
[O:1]=[C:2]1[C:7]([C:8](=[O:16])[NH:9][C:10]2[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=2)=[CH:6][CH:5]=[CH:4][N:3]1[CH:17]1[C:25]2[CH:24]=[CH:23][CH:22]=[C:21]([C:26](O)=[O:27])[C:20]=2[CH2:19][CH2:18]1.CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1.CCN(CC)CC.[CH3:58][NH2:59].Cl>C(Cl)Cl.O>[CH3:58][NH:59][C:26]([C:21]1[CH:22]=[CH:23][CH:24]=[C:25]2[C:20]=1[CH2:19][CH2:18][CH:17]2[N:3]1[CH:4]=[CH:5][CH:6]=[C:7]([C:8]([NH:9][C:10]2[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=2)=[O:16])[C:2]1=[O:1])=[O:27]

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 6364545Methylamine hydrochlorideHCID 66610329HCID 66610329, compound

Product 1

HCID 58102836HCID 58102836, compoundYield 39%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a mixture of 1-(2-oxo-3-(pyridin-4-ylcarbamoyl)pyridin-1(2H)-yl)-2,3-dihydro-1H-indene-4-carboxylic acid (45 mg, 1.0 eq) in DCM (4 mL) was added EDC.HCl (1.5 eq), HOBt (1.5 eq), Et3N (3.0 eq) and MeNH2.HCl (1.1 eq) The mixture was stirred at room temperature overnight. Water was added and the mixture was extracted with DCM. The combined organic layer was washed with brine and dried over MgSO4, evaporated the filtrate to give the crude product, which was purified by HPLC to afford 1-(4-(methylcarbamoyl)-2,3-dihydro-1H-inden-1-yl)-2-oxo-N-(pyridin-4-yl)-1,2-dihydropyridine-3-carboxamide (18 mg, 39%). 389.2 (M+H); 1H NMR (300 MHz, DMSO-d6) δ 12.97 (s, 1H), 8.73 (d, J=3.6 Hz, 2H), 8.51 (dd, J=1.2 Hz, 4.2 Hz, 1H), 8.31 (d, J=2.8 Hz, 1H), 8.20 (d, J=3.6 Hz, 2H), 7.74 (d, J=4.2 Hz, 1H), 7.60 (d, J=4.2 Hz, 1H), 7.35 (t, J=4.2 Hz, 1H), 7.27 (d, J=4.2 Hz, 2H), 6.65 (t, J=4.2 Hz, 1H), 6.55 (t, J=4.2 Hz, 1H), 3.37 (overlap with DMSO-d6, 2H), 2.60-2.75 (m, 1H), 2.05-2.15 (m, 1H).

Workup

  1. extractionthe mixture was extracted with DCM
  2. washThe combined organic layer was washed with brine
  3. dry with materialdried over MgSO4
  4. customevaporated the filtrate
  5. customto give the crude product, which
  6. customwas purified by HPLC

Sources & evidence

ORD record
ord-aff4fff75f0b42a2881a4a522b6d59eb
Source dataset
uspto-grants-2013_02
Patent number
US08367836B2

Reaction notes

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