Trifluoroacetic acid → HCID 58456274, compound

HRID 1040041Notes

Reaction equation

HRID 1040041 reaction equation
C1C2C(OC([NH:17][C:18]3([C:48]([OH:50])=[O:49])[CH2:23][CH2:22][C:21]([OH:47])([C:24]4[S:25][C:26]([C:29]5[CH:34]=[C:33]([NH:35][C:36]6[N:41]=[C:40]([C:42]([F:45])([F:44])[F:43])[CH:39]=[CH:38][N:37]=6)[CH:32]=[C:31]([CH3:46])[CH:30]=5)=[CH:27][N:28]=4)[CH2:20][CH2:19]3)=O)C3C(=CC=CC=3)C=2C=CC=1.N1CCCCC1.C(O)(C(F)(F)F)=O>CN(C=O)C>[NH2:17][C:18]1([C:48]([OH:50])=[O:49])[CH2:23][CH2:22][C:21]([OH:47])([C:24]2[S:25][C:26]([C:29]3[CH:34]=[C:33]([NH:35][C:36]4[N:41]=[C:40]([C:42]([F:45])([F:44])[F:43])[CH:39]=[CH:38][N:37]=4)[CH:32]=[C:31]([CH3:46])[CH:30]=3)=[CH:27][N:28]=2)[CH2:20][CH2:19]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 8082PiperidineHCID 67433394HCID 67433394, compound

Product 1

HCID 58456274HCID 58456274, compoundYield 9.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1-{[(9H-Fluoren-9-yloxy)carbonyl]amino}-4-hydroxy-4-[5-(3-methyl-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)-1,3-thiazol-2-yl]cyclohexanecarboxylic acid (0.079 g, 0.11 mmol) was dissolved in DMF (1.0 mL). Piperidine (0.086 g, 1.01 mmol) was added. After 15 minutes, the reaction mixture was directly purified by reverse phase HPLC to yield 1-amino-4-hydroxy-4-[5-(3-methyl-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)-1,3-thiazol-2-yl]cyclohexanecarboxylic acid (0.005 g, 0.01 mmol) as its TFA salt. MS ESI: [M+H]+ m/z 494.1. 1H NMR (600 MHz, CD3OD) δ 8.70 (d, J=4.9, 1H), 8.04 (s, 1H), 7.94-7.80 (m, 2H), 7.69 (d, J=7.6, 1H), 7.52-7.42 (m, 1H), 7.42-7.34 (m, 1H), 7.18-7.00 (m, 2H), 2.60-2.42 (m, 2H), 2.36 (s, 3H), 2.28-2.07 (m, 4H), 2.05-1.89 (m, 2H). rhSYK activity=+++. The starting material was prepared generally following the procedures described in Examples 32 and 33 using commercially available 1-{[{9H-fluoren-9-ylmethoxy)carbonyl]amino}-4-oxocyclohexanecarboxylic acid.

Workup

  1. customthe reaction mixture was directly purified by reverse phase HPLC

Sources & evidence

ORD record
ord-a648a1c6625a4818a01e57960d2dfe3c
Source dataset
uspto-grants-2013_10
Patent number
US08551984B2

Reaction notes

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