1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 67997233, compound

HRID 1467317Notes

Reaction equation

HRID 1467317 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([C:17]([OH:19])=O)[CH:15]=3)[NH:10][N:9]=2)[CH:5]=[CH:4][N:3]=1.[NH2:20][CH:21]1[CH2:26][CH2:25][CH2:24][N:23]([CH2:27][C:28]2[C:33]([O:34][CH3:35])=[CH:32][CH:31]=[CH:30][C:29]=2[F:36])[C:22]1=[O:37].C(N=C=NCCCN(C)C)C.OC1C2N=NNC=2C=CC=1.C(N(CC)C(C)C)(C)C>CN(C=O)C>[F:36][C:29]1[CH:30]=[CH:31][CH:32]=[C:33]([O:34][CH3:35])[C:28]=1[CH2:27][N:23]1[CH2:24][CH2:25][CH2:26][CH:21]([NH:20][C:17]([C:14]2[CH:15]=[C:16]3[C:11](=[CH:12][CH:13]=2)[NH:10][N:9]=[C:8]3[C:6]2[CH:5]=[CH:4][N:3]=[C:2]([CH3:1])[CH:7]=2)=[O:19])[C:22]1=[O:37]

Participants

7

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 81531DiisopropylethylamineHCID 67995855HCID 67995855, compoundHCID 67996724HCID 67996724, compoundHCID 178418300HCID 178418300, compound

Product 1

HCID 67997233HCID 67997233, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
23 °C

Procedure

3-(2-methylpyridin-4-yl)-1H-indazole-5-carboxylic acid (50 mg, 0.154 mmol), 3-amino-1-(2-fluoro-6-methoxybenzyl)piperidin-2-one (148 mg, 0.308 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (44.4 mg, 0.231 mmol) and hydroxybenzo-triazole (23.62 mg, 0.154 mmol) were combined in a sealed vial. DMF (0.8 ml) and N,N-diisopropylethylamine (0.269 ml, 1.542 mmol) were added and the reaction mixture stirred for 16 hours at a temperature of 23° C. The residue was then purified by preparative HPLC Normal phase, eluting with dichloromethane/MeOH (0-20%) to give N-(1-(2-fluoro-6-methoxybenzyl)-2-oxopiperidin-3-yl)-3-(2-methylpyridin-4-yl)-1H-indazole-5-carboxamide as a colorless solid. MS ESI calc'd. for C27H26FN5O3 [M+H]+488, found 488. 1H NMR (600 MHz, CDCl3) δ 10.80-10.49 (m, 1H), 8.60 (d, J=5.1 Hz, 1H), 8.53 (s, 1H), 7.85 (d, J=8.8 Hz, 1H), 7.73 (s, 1H), 7.67 (d, J=4.9 Hz, 1H), 7.52 (d, J=8.7 Hz, 1H), 7.46 (s, 1H), 6.75-6.65 (m, 3H), 5.00 (d, J=14.1 Hz, 1H), 4.51 (d, J=14.2 Hz, 1H), 4.49-4.42 (m, 1H), 3.84 (s, 3H), 3.35-3.21 (m, 2H), 2.65 (s, 3H), 1.95-1.82 (m, 2H), 1.65-1.55 (s, 2H).

Workup

  1. customThe residue was then purified by preparative HPLC Normal phase
  2. washeluting with dichloromethane/MeOH (0-20%)

Sources & evidence

ORD record
ord-a703ca4900b74b9ea82b23463ae75135
Source dataset
uspto-grants-2015_04
Patent number
US08999957B2

Reaction notes

Loading…