Hydrochloric Acid → HCID 68460811, compound

HRID 2387505Notes

Reaction equation

HRID 2387505 reaction equation
[O:1]=[C:2]1[CH:7]=[C:6]([CH2:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:5]=[CH:4][N:3]1[C:16]1[CH:17]=[C:18]2[C:22](=[CH:23][CH:24]=1)[N:21]([CH2:25][CH2:26][N:27]1[CH2:32][CH2:31][N:30](C(OC(C)(C)C)=O)[CH2:29][CH2:28]1)[N:20]=[CH:19]2.[ClH:40].C(Cl)[Cl:42]>CO.CCOCC>[ClH:42].[ClH:40].[CH2:8]([C:6]1[CH:5]=[CH:4][N:3]([C:16]2[CH:17]=[C:18]3[C:22](=[CH:23][CH:24]=2)[N:21]([CH2:25][CH2:26][N:27]2[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]2)[N:20]=[CH:19]3)[C:2](=[O:1])[CH:7]=1)[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 59293386HCID 59293386, compound

Product 1

HCID 68460811HCID 68460811, compoundYield 69%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

A solution of tert-butyl 4-(2-(5-(2-oxo-4-phenethylpyridin-1(2H)-yl)-1H-indazol-1-yl)ethyl)piperazine-1-carboxylate (247 mg, 0.468 mmol) in MeOH (2 mL) was treated with 2N HCl in ether (7 mL) under a nitrogen atmosphere. The solution was stirred at room temperature for 2 h and then treated with CH2Cl2 (20 mL) to precipitate product. The liquid was decanted off, and the solids were triturated with ether (3×100 mL) and concentrated to yield the title compound (161.7 mg, 69%) as yellow solid: mp 280-290° C.; 1H NMR (500 MHz, CD3OD) δ 8.23 (s, 1H), 7.83 (s, 2H), 7.62 (d, J=6.95 Hz, 1H), 7.46 (d, J=1.4 Hz, 1H), 7.30-7.17 (m, 5H), 6.51 (dd, J=7.0, 1.1 Hz, 1H), 6.48 (s, 1H), 4.95 (t, J=5.85, 2H), 3.57 (m, 2H), 3.61-3.56 (m, 8H), 3.01-2.98 (m, 2H), 2.94-2.91 (m, 2H); ESI MS m/z 428 [M+H]+. HPLC (Method D) 95.4% (AUC), tR=12.9 min.

Workup

  1. customto precipitate product
  2. customThe liquid was decanted off
  3. customthe solids were triturated with ether (3×100 mL)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-e189344a931943dc8e2a1ec4b483c0d6
Source dataset
uspto-grants-2012_09
Patent number
US08268868B2

Reaction notes

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