Trifluoroacetic acid → HCID 49779680, compound

HRID 1808487Notes

Reaction equation

HRID 1808487 reaction equation
C(O)(C(F)(F)F)=O.[C:8]1([C:14]2[CH:15]=[C:16]([C:20]3[N:29]=[C:28]([NH:30][C:31]4[CH:32]=[C:33]5[C:37](=[CH:38][CH:39]=4)[N:36](C([O-])=O)[N:35]=[CH:34]5)[C:27]4[C:22](=[CH:23][C:24]([O:53][CH3:54])=[C:25]([O:43][CH2:44][CH2:45][N:46]5[CH2:51][CH2:50][N:49]([CH3:52])[CH2:48][CH2:47]5)[CH:26]=4)[N:21]=3)[CH:17]=[CH:18][CH:19]=2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>>[C:8]1([C:14]2[CH:15]=[C:16]([C:20]3[N:29]=[C:28]([NH:30][C:31]4[CH:32]=[C:33]5[C:37](=[CH:38][CH:39]=4)[NH:36][N:35]=[CH:34]5)[C:27]4[C:22](=[CH:23][C:24]([O:53][CH3:54])=[C:25]([O:43][CH2:44][CH2:45][N:46]5[CH2:47][CH2:48][N:49]([CH3:52])[CH2:50][CH2:51]5)[CH:26]=4)[N:21]=3)[CH:17]=[CH:18][CH:19]=2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 866424085-(2-[(3-phenyl)phenyl)-7-methoxy-6-(2-(4-methylpiperazin-1-yl)ethoxy)quinazolin-4-ylamino)-1H-indazole-1-carboxylate

Product 1

HCID 49779680HCID 49779680, compoundYield 64%

Procedure

TFA (4 mL) was added to 5-(2-[(3-phenyl)phenyl)-7-methoxy-6-(2-(4-methylpiperazin-1-yl)ethoxy)quinazolin-4-ylamino)-1H-indazole-1-carboxylate and the reaction was stirred at RT for 1.5 h. The solution was concentrated in vacuo and the crude product was triturated with ether and filtered, dried under vacuum to give 2-[(3-phenyl)phenyl)-N-(1H-indazol-5-yl)-7-methoxy-6-(2-(4-methylpiperazin-1-yl)ethoxy)quinazolin-4-amine (0.166 g, 0.283 mmole, 64% over two steps). MS 586.4 (M+1). HPLC retention time 5.06 mins.

Workup

  1. concentrationThe solution was concentrated in vacuo
  2. customthe crude product was triturated with ether
  3. filtrationfiltered
  4. customdried under vacuum

Sources & evidence

ORD record
ord-96b2c799425a4f4dbd5dfdbf2cecf524
Source dataset
uspto-grants-2013_01
Patent number
US08357693B2

Reaction notes

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