Trifluoroacetic acid → HCID 72325456, compound

HRID 1695907Notes

Reaction equation

HRID 1695907 reaction equation
[CH2:1]([N:6]1[C:10](=[O:11])[C:9](=[CH:12][C:13]([OH:15])=O)[S:8][CH:7]1[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH2:2][CH:3]([CH3:5])[CH3:4].[NH:22]1[CH2:27][CH2:26][CH:25]([N:28]2[CH2:37][C:36]3[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=3)[NH:30][C:29]2=[O:38])[CH2:24][CH2:23]1.C(O)(C(F)(F)F)=O.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])[C:9](=[CH:12][C:13]([N:22]2[CH2:23][CH2:24][CH:25]([N:28]3[CH2:37][C:36]4[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=4)[NH:30][C:29]3=[O:38])[CH2:26][CH2:27]2)=[O:15])[S:8][CH:7]1[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH2:2][CH:3]([CH3:4])[CH3:5]

Participants

7

Reactant 5

HCID 6422Trifluoroacetic acidHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 110425973-(Piperidin-4-yl)-3,4-dihydroquinazolin-2(1H)-oneHCID 723254372-(3-Isopentyl-4-oxo-2-phenylthiazolidin-5-ylidene)acetic acid

Product 1

HCID 72325456HCID 72325456, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-(3-isopentyl-4-oxo-2-phenylthiazolidin-5-ylidene)acetic acid (11 mg, 0.036 mmol), 3,4-Dihydro-3-(piperidin-4-yl)quinazolin-2(1H)-one.TFA (18 mg, 0.054 mmol) and DiPEA (22 ul, 0.14 mmol) in DMF (0.2 ml) was added HATU (16 mg, 0.043 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-01463a4452de49d098002912617a2361
Source dataset
uspto-grants-2012_04
Patent number
US08163737B2

Reaction notes

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