Diisopropylethylamine → HCID 59554867, compound

HRID 1695901Notes

Reaction equation

HRID 1695901 reaction equation
[CH:1]([N:4]1[C:8](=[O:9])[CH:7]([CH2:10][C:11]([OH:13])=O)[S:6][CH:5]1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([CH3:3])[CH3:2].[NH:20]1[CH2:25][CH2:24][CH:23]([N:26]2[C:30]3[CH:31]=[CH:32][CH:33]=[CH:34][C:29]=3[NH:28][C:27]2=[O:35])[CH2:22][CH2:21]1.[CH3:36]CN(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>[CH:1]([N:4]1[C:8](=[O:9])[CH:7]([CH2:10][C:11]([N:20]2[CH2:25][CH2:24][CH:23]([N:26]3[CH2:36][C:30]4[C:29](=[CH:34][CH:33]=[CH:32][CH:31]=4)[NH:28][C:27]3=[O:35])[CH2:22][CH2:21]2)=[O:13])[S:6][CH:5]1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([CH3:2])[CH3:3]

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 59555338HCID 59555338, compound

Product 1

HCID 59554867HCID 59554867, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolvent

Procedure

To a solution of 2-(3-isopropyl-4-oxo-2-phenylthiazolidin-5-yl)acetic acid (0.2 mmol, 56 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)=493.5; tR=3.1. 1H NMR (400 MHz, CDCl3) δ 7.31-7.25 (m, 5H), 7.14-7.10 (m, 1H), 7.05 (s, 1H), 7.00 (m, 1H), 6.93-6.89 (m, 1H), 6.62 (d, J=7.8 Hz, 1H), 5.56 (m, 1H), 4.72 (m, 1H), 4.47-4.41 (m, 2H), 4.27-4.19 (m, 2H), 4.02-3.96 (m, 1H), 3.87 (m, 1H), 3.36-3.29 (m, 1H), 3.13-3.10 (m, 1H), 2.70 (m, 2H), 1.70-1.60 (m, 3H), 1.20 (dd, J=2.0, 6.9 Hz, 3H), 0.94 (m, 3H).

Workup

  1. customPurification by preparative reverse phase

Sources & evidence

ORD record
ord-1073915087ab4f84bbc197994b3fc97c
Source dataset
uspto-grants-2012_04
Patent number
US08163737B2

Reaction notes

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