Trifluoroacetic acid → Phenylmethyl 4-[(4-chloro-1H-pyrrolo[3,2-c]pyridin-2-yl)methyl]-3-oxo-1-piperazinecarboxylate

HRID 1432951Notes

Reaction equation

HRID 1432951 reaction equation
FC(F)(F)C(O)=O.C(OC([N:15]1[C:23]2[CH:22]=[CH:21][N:20]=[C:19]([Cl:24])[C:18]=2[CH:17]=[C:16]1[CH2:25][N:26]1[CH2:31][CH2:30][N:29]([C:32]([O:34][CH2:35][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)=[O:33])[CH2:28][C:27]1=[O:42])=O)(C)(C)C>C(Cl)Cl>[CH2:35]([O:34][C:32]([N:29]1[CH2:30][CH2:31][N:26]([CH2:25][C:16]2[NH:15][C:23]3[CH:22]=[CH:21][N:20]=[C:19]([Cl:24])[C:18]=3[CH:17]=2)[C:27](=[O:42])[CH2:28]1)=[O:33])[C:36]1[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86760978HCID 86760978, compound

Product 1

HCID 53757606Phenylmethyl 4-[(4-chloro-1H-pyrrolo[3,2-c]pyridin-2-yl)methyl]-3-oxo-1-piperazinecarboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Trifluoroacetic acid (10 mL) is added to a solution of 2-(4-benzyloxycarbonyl-2-oxo-piperazin-1-ylmethyl)-4-chloro-pyrrolo[3,2-c]pyridine-1-carboxylic acid tert-butyl ester (5.66 g, 11.3 mmol, prepared in the same manner as described previously) in CH2Cl2 (10 mL). The solution is stirred overnight then diluted with CH2Cl2 and washed with saturated NaHCO3 and brine. The organic layer is dried over MgSO4, filtered and concentrated to dryness. The crude product is chromatographed eluting with 1-5% MeOH/CH2Cl2 to yield the title product (3.81 g, 9.56 mmol) as a foamy yellow solid. 1H NMR (CDCl3, 300 MHz) δ9.43 (bs, 1H), 8.08 (d, 1H), 7.38 (s, 5H), 7.18 (d, 1H), 6.51 (s, 1H), 5.15 (s, 2H), 4.58 (s, 2H), 4.20 (s, 2H), 3.71 (m, 2H), 3.50 (m, 2H). Ion spray [M+H]+=399, 401, Cl pattern.

Workup

  1. customprepared in the same manner
  2. washwashed with saturated NaHCO3 and brine
  3. dry with materialThe organic layer is dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated to dryness
  6. customThe crude product is chromatographed
  7. washeluting with 1-5% MeOH/CH2Cl2

Sources & evidence

ORD record
ord-89c763872df94fb49082851a202ac181
Source dataset
uspto-grants-2009_11
Patent number
US07612075B2

Reaction notes

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