HCID 178452222, compound → HCID 178509861, compound

HRID 1909043Notes

Reaction equation

HRID 1909043 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[N:19]=[C:18]3[NH:20][C:21]([C:23](=[O:42])[C:24]4[CH:29]=[CH:28][C:27]([C:30]#[N:31])=[C:26]([C:32]5[C:41]6[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=6)[CH:35]=[N:34][CH:33]=5)[CH:25]=4)=[N:22][C:17]3=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)=O)(C)(C)C>Cl.C(OCC)C>[CH:35]1[C:36]2[C:41](=[CH:40][CH:39]=[CH:38][CH:37]=2)[C:32]([C:26]2[CH:25]=[C:24]([C:23]([C:21]3[NH:20][C:18]4=[N:19][C:14]([N:11]5[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]5)=[CH:15][CH:16]=[C:17]4[N:22]=3)=[O:42])[CH:29]=[CH:28][C:27]=2[C:30]#[N:31])=[CH:33][N:34]=1

Participants

3

Reactant 1

HCID 178452222HCID 178452222, compound

Product 1

HCID 178509861HCID 178509861, compoundYield 34.5%

Reagents, catalysts & solvents 1

HCID 10953452Ether hydrochlorideSolvent

Procedure

4-[2-(4-cyano-3-isoquinolin-4-yl-benzoyl)-3H-imidazo[4,5-b]pyridine-5-yl]piperazine-1-carboxylic acid tert-butyl ester solution (16 mg, 0.029 mmole) in 2 M HCl ethylether (2 ml) was stirred at room temperature for 1 hour. Solvent was removed. Solid was washed with ether for three times and purified by using HPLC (20% to 100% acetonitrile in water with 0.1% NH4OH) to afford product (4.6 mg, 25%) as a yellow solid. 1H NMR (400 MHz, CD2Cl2) δ 2.86 (m, 4H), 3.55 (m, 4H), 6.73 (d, J=9.03 Hz, 1H), 7.59 (d, J=8.03 Hz, 1H), 7.66 (m, 2H), 8.00 (d, J=9.03 Hz, 1H), 7.97 (d, J=8.03 Hz, 1H), 8.07 (d, J=8.03 Hz, 1H), 8.50 (s, 1H), 8.72 (s, 1H), 8.77 (d, J=8.03 Hz, 1H), 9.31 (s, 1H). HR-MS m/z 460.1896 (M+1).

Workup

  1. customSolvent was removed
  2. washSolid was washed with ether for three times
  3. custompurified

Sources & evidence

ORD record
ord-4c48a73e277d4f348a679a6741417d6c
Source dataset
uspto-grants-2013_12
Patent number
US08598217B2

Reaction notes

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