Trifluoroacetic acid → HCID 67045092, compound

HRID 1034780Notes

Reaction equation

HRID 1034780 reaction equation
[Br:1][C:2]1[C:3]([N:22]2[CH2:27][CH2:26][CH2:25][C@@H:24]([NH:28]C(=O)OC(C)(C)C)[CH2:23]2)=[C:4]2[C:10]([NH:11][C:12](=[O:21])[C:13]3[CH:18]=[CH:17][C:16]([F:19])=[C:15]([Cl:20])[CH:14]=3)=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[ClH:20].[NH2:28][C@@H:24]1[CH2:25][CH2:26][CH2:27][N:22]([C:3]2[C:2]([Br:1])=[CH:7][N:6]=[C:5]3[NH:8][CH:9]=[C:10]([NH:11][C:12](=[O:21])[C:13]4[CH:18]=[CH:17][C:16]([F:19])=[C:15]([Cl:20])[CH:14]=4)[C:4]=23)[CH2:23]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67045184HCID 67045184, compound

Product 1

HCID 67045092HCID 67045092, compoundYield 163.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of (R)-tert-butyl 1-(5-bromo-3-(3-chloro-4-fluorobenzamido)-1H-pyrrolo[2,3-b]pyridin-4-yl)piperidin-3-ylcarbamate (110 mg, 0.194 mmol) in DCM (3 mL) was treated with TFA (1 mL) at room temperature for 1 hour. The mixture was then concentrated in vacuo. The resulting residue was dissolved in a minimal amount of DCM and added to a stirring solution of 1M HCl in ether. The solid obtained was filtered, washed with ether and dried to provide (R)—N-(4-(3-aminopiperidin-1-yl)-5-bromo-1H-pyrrolo[2,3-b]pyridin-3-yl)-3-chloro-4-fluorobenzamide hydrochloride (80 mg, 76% yield). 1H NMR (400 MHz, D2O) δ 8.22 (s, 1H), 7.97-7.94 (m, 1H), 7.80-7.77 (m, 1H), 7.38 (s, 1H), 7.32-7.28 (m, 1H), 3.54-3.52 (m, 1H), 3.32-3.30 (m, 1H), 3.25-3.21 (m, 1H), 3.18-3.10 (m, 2H), 1.88-1.80 (m, 1H), 1.68-1.63 (m, 1H), 1.50-1.33 (m, 2H); LCMS (APCI+) m/z 466, 486 (M+H)+.

Workup

  1. concentrationThe mixture was then concentrated in vacuo
  2. dissolutionThe resulting residue was dissolved in a minimal amount of DCM
  3. additionadded to a stirring solution of 1M HCl in ether
  4. customThe solid obtained
  5. filtrationwas filtered
  6. washwashed with ether
  7. customdried

Sources & evidence

ORD record
ord-6dcb9f9a4abf4d8bba969ff057da1eab
Source dataset
uspto-grants-2013_10
Patent number
US08545897B2

Reaction notes

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