HCID 68184860, compound → HCID 68161437, compound

HRID 2041750Notes

Reaction equation

HRID 2041750 reaction equation
[C:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([C:14]3[CH:15]=[N:16][N:17]([CH2:19][CH2:20][N:21](C)[C:22](=O)OC(C)(C)C)[CH:18]=3)=[CH:11][CH:12]=2)[C@H:7]([NH:30][C:31]2[CH:32]=[N:33][CH:34]=[CH:35][CH:36]=2)[CH2:6][C@@H:5]1[CH3:37])(=[O:3])[CH3:2]>ClCCl>[C:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([C:14]3[CH:15]=[N:16][N:17]([CH2:19][CH2:20][NH:21][CH3:22])[CH:18]=3)=[CH:11][CH:12]=2)[C@H:7]([NH:30][C:31]2[CH:32]=[N:33][CH:34]=[CH:35][CH:36]=2)[CH2:6][C@@H:5]1[CH3:37])(=[O:3])[CH3:2]

Participants

3

Reactant 1

HCID 68184860HCID 68184860, compound

Product 1

HCID 68161437HCID 68161437, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 1,1-dimethylethyl (2-{4-[(2S,4R)-1-acetyl-2-methyl-4-(3-pyridinylamino)-1,2,3,4-tetrahydro-6-quinolinyl]-1H-pyrazol-1-yl}ethyl)methylcarbamate (for a preparation see intermediate 58) (84 mg, 0.166 mmol) in dichloromethane (DCM) (3 mL) at room temperature under nitrogen was treated with trifluoroacteic acid TFA (0.5 mL, 6.49 mmol) and the resulting mixture was stirred at this temperature for 1 h then concentrated in vacuo. The residue was loaded onto a 10 G SCX cartridge and eluted with MeOH (2×20 mL) then with a 2N NH3 in MeOH (20 mL). The ammonia fractions were collected and concentrated in vacuo to give (2S,4R)-1-acetyl-2-methyl-6-{1-[2-(methylamino)ethyl]-1H-pyrazol-4-yl}-N-3-pyridinyl-1,2,3,4-tetrahydro-4-quinolinamine (61 mg, 0.151 mmol, 91%) as a brown oil.

Workup

  1. customat room temperature
  2. concentrationthen concentrated in vacuo
  3. washeluted with MeOH (2×20 mL)
  4. customThe ammonia fractions were collected
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2f3ed72a52ad496cb50b09ae40c6c433
Source dataset
uspto-grants-2013_11
Patent number
US08580957B2

Reaction notes

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