Trifluoroacetic acid → HCID 49779680, compound

HRID 61625Notes

Reaction equation

HRID 61625 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-ed1e2bdb01f440f68adfb6a9c48e0b2e
Source dataset
uspto-grants-2016_09
Patent number
US09440961B2

Reaction notes

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