Trifluoroacetic acid → HCID 58346593, compound

HRID 222048Notes

Reaction equation

HRID 222048 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:17][C:18]2[C:23]3[C:24]4[CH2:32][CH2:31][C:30]5[C:26](=[CH:27][N:28]([CH:33]6[CH2:38][CH2:37][N:36](C(OC(C)(C)C)=O)[CH2:35][CH2:34]6)[N:29]=5)[C:25]=4[S:46][C:22]=3[N:21]=[CH:20][N:19]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([F:16])[CH:11]=1.FC(F)(F)C(O)=O>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([NH:17][C:18]2[N:19]=[CH:20][N:21]=[C:22]3[S:46][C:25]4[C:26]5[C:30]([CH2:31][CH2:32][C:24]=4[C:23]=23)=[N:29][N:28]([CH:33]2[CH2:38][CH2:37][NH:36][CH2:35][CH2:34]2)[CH:27]=5)[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([F:16])[CH:11]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58346494HCID 58346494, compound

Product 1

HCID 58346593HCID 58346593, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of tert-butyl 4-[6-({3-chloro-4-[(3-fluorobenzyl)oxy]phenyl}amino)-4,5-dihydro-2H-pyrimido[5′,4′:4,5]thieno[2,3-e]indazol-2-yl]piperidine-1-carboxylate 1.2 g (1.8 mmol, 1 eq) in DCM (40 mL) was added trifluoroacetic acid (4.2 mL, 30 eq). The reaction mixture was stirred at rt for 3 h. The Volatile material was evaporated and the residue was diluted with EtOAc. Sat. Na2CO3 was added until pH about 7. The layers were separated and the aqueous layer was extracted with EtOAc (3 times) and the combined organic layers were concentrated to give a brown solid (1 g, quantitative). 1H-NMR (DMSO-d6) δ 8.41 (s, 1H), 8.33 (s, 1H), 8.01 (s, 1H), 7.74 (d, 1H), 7.47 (m, 2H), 7.30 (m, 2H), 7.20 (m, 2H), 5.24 (s, 2H), 4.25 (m, 1H), 3.40 (t, 2H), 3.18 (m, 2H), 2.93 (t, 2H), 2.76 (t, 2H), 2.05 (m, 2H), 1.91 (m, 2H). LCMS RT=2.83 min; [M+H]+=561.2.

Workup

  1. customThe Volatile material was evaporated
  2. additionthe residue was diluted with EtOAc
  3. additionSat. Na2CO3 was added until pH about 7
  4. customThe layers were separated
  5. extractionthe aqueous layer was extracted with EtOAc (3 times)
  6. concentrationthe combined organic layers were concentrated
  7. customto give a brown solid (1 g, quantitative)

Sources & evidence

ORD record
ord-78a9b4e46d17442592ab2c8b927cb3c1
Source dataset
uspto-grants-2012_06
Patent number
US08207172B2

Reaction notes

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