Trifluoroacetic acid → HCID 59415836, compound

HRID 2061818Notes

Reaction equation

HRID 2061818 reaction equation
[CH3:1][O:2][CH2:3][CH:4]([N:8]1[C:17]2[C:12](=[CH:13][C:14]([C:18]3[CH:19]=[N:20][C:21]([NH:33][C:34](=[O:38])[NH:35][CH2:36][CH3:37])=[CH:22][C:23]=3[C:24]3[S:25][CH:26]=[C:27]([C:29]([F:32])([F:31])[F:30])[N:28]=3)=[CH:15][CH:16]=2)[C:11](=[O:39])[C:10]([C:40]([N:42]2[CH2:47][CH2:46][N:45](C(OC(C)(C)C)=O)[CH2:44][CH2:43]2)=[O:41])=[CH:9]1)[CH2:5][O:6][CH3:7].FC(F)(F)C(O)=O>ClCCl>[CH3:7][O:6][CH2:5][CH:4]([N:8]1[C:17]2[C:12](=[CH:13][C:14]([C:18]3[C:23]([C:24]4[S:25][CH:26]=[C:27]([C:29]([F:32])([F:30])[F:31])[N:28]=4)=[CH:22][C:21]([NH:33][C:34]([NH:35][CH2:36][CH3:37])=[O:38])=[N:20][CH:19]=3)=[CH:15][CH:16]=2)[C:11](=[O:39])[C:10]([C:40]([N:42]2[CH2:43][CH2:44][NH:45][CH2:46][CH2:47]2)=[O:41])=[CH:9]1)[CH2:3][O:2][CH3:1]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 44540258HCID 44540258, compound

Product 1

HCID 59415836HCID 59415836, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Tert-butyl 4-{[1-(1,3-dimethoxypropan-2-yl)-6-{6-[(ethylcarbamoyl)amino]-4-[4-(trifluoromethyl)-1,3-thiazol-2-yl]pyridin-3-yl}-4-oxo-1,4-dihydroquinolin-3-yl]carbonyl}piperazine-1-carboxylate (Example 139, 260 mg, 0.33 mmol) was dissolved in dichloromethane (15 mL). Trifluoroacetic acid (195 mg, 1.68 mmol) was added to the mixture and it was stirred for 30 h at room temperature. The reaction mixture was concentrated, and the pH was adjusted to 8 with saturated sodium bicarbonate solution to give solid compound which was filtered and dried to afford 160 mg (72%) of 1-{5-[1-(1,3-dimethoxypropan-2-yl)-4-oxo-3-(piperazin-1-ylcarbonyl)-1,4-dihydroquinolin-6-yl]-4-[4-(trifluoromethyl)-1,3-thiazol-2-yl]pyridin-2-yl}-3-ethylurea.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customto give solid compound which
  3. filtrationwas filtered
  4. customdried

Sources & evidence

ORD record
ord-fd524f4432ff4156b69ced0db76201d5
Source dataset
uspto-grants-2012_10
Patent number
US08283361B2

Reaction notes

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