Diisopropylethylamine → 1-(1-(2-(4-Oxo-2-phenyl-3-((pyridin-4-yl)methyl)thiazolidin-5-yl)acetyl)piperidin-4-yl)-1H-benzo[d]imidazol-2(3H)-one

HRID 1172298Notes

Reaction equation

HRID 1172298 reaction equation
[O:1]=[C:2]1[CH:6]([CH2:7][C:8](O)=[O:9])[S:5][CH:4]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[N:3]1[CH2:17][C:18]1[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=1.[NH:24]1[CH2:29][CH2:28][CH:27]([N:30]2[C:34]3[CH:35]=[CH:36][CH:37]=[CH:38][C:33]=3[NH:32][C:31]2=[O:39])[CH2:26][CH2:25]1.CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C.CC#N>[O:1]=[C:2]1[CH:6]([CH2:7][C:8]([N:24]2[CH2:25][CH2:26][CH:27]([N:30]3[C:34]4[CH:35]=[CH:36][CH:37]=[CH:38][C:33]=4[NH:32][C:31]3=[O:39])[CH2:28][CH2:29]2)=[O:9])[S:5][CH:4]([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)[N:3]1[CH2:17][C:18]1[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 886381,3-Dihydro-1-(4-piperidinyl)-2H-benzimidazol-2-oneHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 595553082-(4-Oxo-2-phenyl-3-((pyridin-4-yl)methyl)thiazolidin-5-yl)acetic acid

Product 1

HCID 595550791-(1-(2-(4-Oxo-2-phenyl-3-((pyridin-4-yl)methyl)thiazolidin-5-yl)acetyl)piperidin-4-yl)-1H-benzo[d]imidazol-2(3H)-one

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolvent

Procedure

To a solution of 2-(4-oxo-2-phenyl-3-((pyridin-4-yl)methyl)thiazolidin-5-yl)acetic acid (0.15 mmol, 49 mg), 1-(piperidin-4-yl)-1H-benzo[d]imidazol-2(3H)-one (0.15 mmol, 33 mg) and DIPEA (0.375 mmol, 65.3 μl) in 4:1 CH3CN:DMF (0.5 ml) was added HATU (0.18 mmol, 68 mg) and the reaction mixture was stirred at room temperature for 16 h. Purification by preparative reverse phase HPLC using 10%/99% CH3CN (0.035% TFA)/H2O (0.05% TFA) gave the title compound. LC/MS (10% to 99%): M/Z (M+H)+ (obs)=528.1; tR=2.28. H NMR (400 MHz, CDCl3) δ 9.00 (s, 1H), 8.60 (d, J=6.3 Hz, 2H), 7.40-7.38 (m, 2H), 7.33-7.29 (m, 5H), 7.06-6.92 (m, 4H), 5.55-5.53 (m, 1H), 4.55 (d, J=4.4 Hz, 2H), 4.45-4.42 (m, 3H), 4.07 (d, m, 2H), 3.42-3.41 (m, 1H), 3.20-3.15 (m, 1H), 3.01-2.90 (m, 1H), 2.66 (m, 2H), 1.88 (m, 2H) ppm.

Workup

  1. customPurification by preparative reverse phase

Sources & evidence

ORD record
ord-d291aae825cb4f70ba8f6de57ae17baa
Source dataset
uspto-grants-2010_11
Patent number
US07834000B2

Reaction notes

Loading…