Diisopropylethylamine → 3-(1-(2-(3-Isopentyl-4-oxo-2-phenylthiazolidin-5-yl)propanoyl)piperidin-4-yl)-3,4-dihydroquinazolin-2(1H)-one

HRID 1172305Notes

Reaction equation

HRID 1172305 reaction equation
[CH2:1]([N:6]1[C:10](=[O:11])[CH:9]([CH:12]([CH3:16])[C:13](O)=[O:14])[S:8][CH:7]1[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH2:2][CH:3]([CH3:5])[CH3:4].OC(C(F)(F)F)=O.[NH:30]1[CH2:35][CH2:34][CH:33]([N:36]2[CH2:45][C:44]3[C:39](=[CH:40][CH:41]=[CH:42][CH:43]=3)[NH:38][C:37]2=[O:46])[CH2:32][CH2:31]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>[CH2:1]([N:6]1[C:10](=[O:11])[CH:9]([CH:12]([CH3:16])[C:13]([N:30]2[CH2:31][CH2:32][CH:33]([N:36]3[CH2:45][C:44]4[C:39](=[CH:40][CH:41]=[CH:42][CH:43]=4)[NH:38][C:37]3=[O:46])[CH2:34][CH2:35]2)=[O:14])[S:8][CH:7]1[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH2:2][CH:3]([CH3:5])[CH3:4]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 595549512-(3-Isopentyl-4-oxo-2-phenylthiazolidin-5-yl)propanoic acidHCID 691875533,4-dihydro-3-(piperidin-4-yl)quinazolin-2(1H)-one TFA

Product 1

HCID 595549023-(1-(2-(3-Isopentyl-4-oxo-2-phenylthiazolidin-5-yl)propanoyl)piperidin-4-yl)-3,4-dihydroquinazolin-2(1H)-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-(3-Isopentyl-4-oxo-2-phenylthiazolidin-5-yl)propanoic acid (11 mg, 0.034 mmol), 3,4-Dihydro-3-(piperidin-4-yl)quinazolin-2(1H)-one TFA (17 mg, 0.051 mmol) and DiPEA (24 ul, 0.14 mmol) in DMF (0.2 ml) was added HATU (17 mg, 0.044 mmol) and the reaction mixture was stirred at RT for 16 hours. Purification by preparative reverse phase HPLC using 10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA) gave the title compound.

Workup

  1. customPurification by preparative reverse phase

Sources & evidence

ORD record
ord-b8fea75e067c43f5a322a91a454413e3
Source dataset
uspto-grants-2010_11
Patent number
US07834000B2

Reaction notes

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