1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 178487652, compound

HRID 578962Notes

Reaction equation

HRID 578962 reaction equation
[OH:1][C:2]1[N:6]([C:7]2[CH:15]=[CH:14][C:10]([C:11](O)=[O:12])=[CH:9][N:8]=2)[N:5]=[CH:4][C:3]=1[C:16]1[CH:21]=[CH:20][N:19]=[C:18]([O:22][CH3:23])[CH:17]=1.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.[O:45]1[CH2:50][CH2:49][CH:48]([CH2:51][NH2:52])[CH2:47][CH2:46]1.CCN(C(C)C)C(C)C>CN(C=O)C>[OH:1][C:2]1[N:6]([C:7]2[CH:15]=[CH:14][C:10]([C:11]([NH:52][CH2:51][CH:48]3[CH2:49][CH2:50][O:45][CH2:46][CH2:47]3)=[O:12])=[CH:9][N:8]=2)[N:5]=[CH:4][C:3]=1[C:16]1[CH:21]=[CH:20][N:19]=[C:18]([O:22][CH3:23])[CH:17]=1

Participants

7

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27732104-AminomethyltetrahydropyranHCID 178487655HCID 178487655, compound

Product 1

HCID 178487652HCID 178487652, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Combined 6-(5-hydroxy-4-(2-methoxypyridin-4-yl)-1H-pyrazol-1-yl)nicotinic acid (30 mg, 0.096 mmol), EDCI (27.6 mg, 0.144 mmol), HOBT (19.47 mg, 0.144 mmol), and DMF (961 μl), then added (tetrahydro-2H-pyran-4-yl)methanamine (17.66 μl, 0.144 mmol) and Hunig's base (68.3 μl, 0.384 mmol) and stirred at room temperature overnight. The reaction mixture was purified via preparative HPLC to give the title compound (32.1 mg, 82%) as a yellow solid. 1H NMR (400 MHz, methanol-d4) δ ppm 1.35 (qd, J=12.38, 4.55 Hz, 2 H) 1.71 (d, J=12.88 Hz, 2 H) 1.84-1.99 (m, 1 H) 3.42 (td, J=11.68, 1.64 Hz, 2 H) 3.95 (d, J=3.28 Hz, 1 H) 3.98 (s, 3 H) 4.19 (s, 3 H) 7.76 (d, J=6.57 Hz, 1 H) 7.84 (s, 1 H) 8.03 (d, J=6.57 Hz, 1 H) 8.28-8.47 (m, 2 H) 8.55 (br. s., 1 H) 8.85 (br. s., 1 H). MS m/z [M+H]+ 410.1.

Workup

  1. customThe reaction mixture was purified via preparative HPLC

Sources & evidence

ORD record
ord-149d8bf038ee4d16b484a2f8c006c0e1
Source dataset
uspto-grants-2015_05
Patent number
US09040522B2

Reaction notes

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