Hydrochloric Acid → HCID 57405171, compound

HRID 1520086Notes

Reaction equation

HRID 1520086 reaction equation
Cl.[CH3:2][N:3]([CH3:43])[CH:4]1[CH2:8][CH2:7][N:6]([C:9]2[CH:10]=[C:11]3[C:15](=[CH:16][CH:17]=2)[N:14](C2CCCCO2)[N:13]=[C:12]3[C:24]2[N:25]=[N:26][N:27]([C:29]3[CH:34]=[CH:33][C:32]([C:35]([N:37]4[CH2:42][CH2:41][O:40][CH2:39][CH2:38]4)=[O:36])=[CH:31][CH:30]=3)[CH:28]=2)[CH2:5]1>O1CCOCC1.C(Cl)Cl.CO>[CH3:2][N:3]([CH3:43])[CH:4]1[CH2:8][CH2:7][N:6]([C:9]2[CH:10]=[C:11]3[C:15](=[CH:16][CH:17]=2)[NH:14][N:13]=[C:12]3[C:24]2[N:25]=[N:26][N:27]([C:29]3[CH:34]=[CH:33][C:32]([C:35]([N:37]4[CH2:42][CH2:41][O:40][CH2:39][CH2:38]4)=[O:36])=[CH:31][CH:30]=3)[CH:28]=2)[CH2:5]1

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 86699015HCID 86699015, compound

Product 1

HCID 57405171HCID 57405171, compoundYield 70.3%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

Hydrogen chloride (0.72 mL of a 4 N solution in dioxane) was added to a solution of N,N-dimethyl-1-[3-{1-[4-(morpholin-4-ylcarbonyl)phenyl]-1H-1,2,3-triazol-4-yl}-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-5-yl]pyrrolidin-3-amine (110 mg; 0.19 mmol; 1.0 eq.) in DCM (1.1 mL) and MeOH (0.55 mL). The reaction mixture was stirred at RT O/N. Solvents were then removed under reduced pressure and the residue was purified by preparative HPLC to give the title compound as a yellow powder (65 mg, 69%). 1H NMR (300 MHz, MeOD): 8.98 (s, 1H), 8.14 (d, J=8.7 Hz, 2H), 7.73 (d, J=8.7 Hz, 2H), 7.53 (d, J=9.1 Hz, 1H), 7.48 (d, J=2.0 Hz, 1H), 7.13 (dd, J=8.1 Hz, 2.0 Hz, 1H), 3.80-3.68 (m, 9H), 3.63-3.43 (m, 4H), 2.84 (s, 6H), 2.61-2.51 (m, 1H), 2.30-2.21 (m, 1H). HPLC (max plot) 96.0%; Rt %2.12 min. UPLC/MS: (MS+) 487.4, (MS−) 485.3.

Workup

  1. customSolvents were then removed under reduced pressure
  2. customthe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-3ced08f87c1a4bd8aa442605b0b61eb7
Source dataset
uspto-grants-2015_07
Patent number
US09073892B2

Reaction notes

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