Trifluoroacetic acid → HCID 42642627, compound

HRID 1676412Notes

Reaction equation

HRID 1676412 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([C:11]2[C:12]([NH:17][C:18]3[CH:46]=[CH:45][C:21]([O:22][C:23]4[CH:28]=[CH:27][N:26]=[C:25]5[CH:29]=[C:30]([CH:32]6[CH2:37][CH2:36][N:35](C(OC(C)(C)C)=O)[CH2:34][CH2:33]6)[S:31][C:24]=45)=[C:20]([F:47])[CH:19]=3)=[N:13][CH:14]=[CH:15][CH:16]=2)=[O:10])=[CH:4][CH:3]=1.C(O)(C(F)(F)F)=O>>[F:47][C:20]1[CH:19]=[C:18]([NH:17][C:12]2[N:13]=[CH:14][CH:15]=[CH:16][C:11]=2[C:9]([NH:8][C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)=[O:10])[CH:46]=[CH:45][C:21]=1[O:22][C:23]1[CH:28]=[CH:27][N:26]=[C:25]2[CH:29]=[C:30]([CH:32]3[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]3)[S:31][C:24]=12

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67347388HCID 67347388, compound

Product 1

HCID 42642627HCID 42642627, compoundYield 96.6%

Procedure

A round-bottomed flask was charged with tert-butyl 4-(7-(4-(3-((4-fluorophenyl)carbamoyl)pyridin-2-ylamino)-2-fluorophenoxy)thieno[3,2-b]pyridin-2-yl)piperidine-1-carboxylate (60 mg, 0.091 mmol) and TFA (3 mL). After stirring at room temperature for 4 hours, the mixture was concentrated under high vacuum and aqueous 1M Na2CO3 (5 mL) was added with stirring. The mixture was then extracted with EtOAc (10 mL) and the organics were isolated and dried over sodium sulfate, filtered and concentrated to get product (49 mg, 96%) as a yellow solid. LRMS (esi+) 558 m/z (M+1) detected.

Workup

  1. concentrationthe mixture was concentrated under high vacuum and aqueous 1M Na2CO3 (5 mL)
  2. additionwas added
  3. stirringwith stirring
  4. extractionThe mixture was then extracted with EtOAc (10 mL)
  5. customthe organics were isolated
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-17b06797384447dfbd0e3a36a7702b5d
Source dataset
uspto-grants-2011_08
Patent number
US08003662B2

Reaction notes

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