Trifluoroacetic acid → HCID 58529326, compound

HRID 1972833Notes

Reaction equation

HRID 1972833 reaction equation
[NH2:1][C:2]1[C:7]2=[C:8]([C:23]3[CH:24]=[CH:25][C:26]4[C:30]([CH:31]=3)=[N:29][N:28]([CH2:32][C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[CH:27]=4)[CH:9]=[C:10]([CH:11]3[CH2:15][CH2:14][N:13](C(OC(C)(C)C)=O)[CH2:12]3)[N:6]2[N:5]=[CH:4][N:3]=1.FC(F)(F)C(O)=O>ClCCl>[CH2:32]([N:28]1[CH:27]=[C:26]2[C:30]([CH:31]=[C:23]([C:8]3[CH:9]=[C:10]([CH:11]4[CH2:15][CH2:14][NH:13][CH2:12]4)[N:6]4[C:7]=3[C:2]([NH2:1])=[N:3][CH:4]=[N:5]4)[CH:24]=[CH:25]2)=[N:29]1)[C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58529330HCID 58529330, compound

Product 1

HCID 58529326HCID 58529326, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a dry flask was added tert-butyl 3-[4-amino-5-(2-benzyl-2H-indazol-6-yl)pyrrolo[2,1-f][1,2,4]triazin-7-yl]pyrrolidine-1-carboxylate (420 mg, 0.824 mmol) followed by a solution of 1:1 trifluoroacetic acid in dichloromethane (3 mL). The mixture was stirred under N2 atmosphere for 1.5 h. The reaction was then partitioned between dichloromethane (150 mL) and 10% aqueous potassium carbonate. The aqueous layer was back extracted with dichloromethane (2×25 mL). The combined organic layer was washed with brine (50 mL) then dried with sodium sulfate. The solvent was evaporated under reduced pressure to yield 320 mg (95%) of the desired product as a tan solid. 1H NMR (300 MHz, DMSO-d6) δ 8.53 (s, 1 H), 7.89 (s, 1 H), 7.78 (d, 1 H), 7.58 (s, 1 H), 7.50-7.30 (m, 4H), 7.14 (d, 1 H), 6.58 (s, 1 H), 5.64 (s, 2 H), 3.98 (m, 1 H), 3.35-3.25 (m, 3 H), 2.10 (m, 1 H), 1.92 (m, 1 H); ES-MS m/z 410.4 [M+H]+, HPLC RT (min) 2.00.

Workup

  1. customThe reaction was then partitioned between dichloromethane (150 mL) and 10% aqueous potassium carbonate
  2. extractionThe aqueous layer was back extracted with dichloromethane (2×25 mL)
  3. washThe combined organic layer was washed with brine (50 mL)
  4. dry with materialthen dried with sodium sulfate
  5. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-90dd62a5675748799e93414e9ddf2c87
Source dataset
uspto-grants-2013_04
Patent number
US08431695B2

Reaction notes

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