Hydrochloric Acid → HCID 67203698, compound

HRID 2366919Notes

Reaction equation

HRID 2366919 reaction equation
CC([O:4][C:5](=[O:42])[NH:6][C@H:7]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([C:17]3[CH:18]=[N:19][N:20]([CH2:22][CH2:23][N:24]4[CH2:29][CH2:28][CH:27]([NH:30]C(OC(C)(C)C)=O)[CH2:26][CH2:25]4)[CH:21]=3)[CH:15]=2)[N:10]([C:38](=[O:40])[CH3:39])[C@@H:9]([CH3:41])[CH2:8]1)C.F[C:44](F)(F)[C:45](O)=O.[ClH:50].[Cl:51][CH2:52]Cl>CO>[ClH:51].[ClH:50].[CH3:52][CH:44]([N:6]([C@H:7]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([C:17]3[CH:18]=[N:19][N:20]([CH2:22][CH2:23][N:24]4[CH2:29][CH2:28][CH:27]([NH2:30])[CH2:26][CH2:25]4)[CH:21]=3)[CH:15]=2)[N:10]([C:38](=[O:40])[CH3:39])[C@@H:9]([CH3:41])[CH2:8]1)[C:5](=[O:42])[OH:4])[CH3:45]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 86669260HCID 86669260, compound

Product 1

HCID 67203698HCID 67203698, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

1-Methylethyl[(cis)-1-acetyl-6-(1-{2-[4-({[(1,1-dimethylethyl)oxy]carbonyl}amino)-1-piperidinyl]ethyl}-1H-pyrazol-4-yl)-2-methyl-1,2,3,4-tetrahydro-4-quinolinyl]carbamate (for a preparation see Intermediate 37) (130 mg, 0.223 mmol) was dissolved in dichloromethane (DCM) (1 mL), mixed with trifluoroacetic acid (0.5 mL, 6.49 mmol) and stirred under nitrogen. The crude product was concentrated and purified on MDAP. The product-containing fractions were evaporated to dryness, loaded onto a 2 g SCX cartridge and eluted with MeOH (15 ml) and 2M methanolic ammonia (15 ml). The basic fractions were evaporated to give a white solid which was dissolved in MeOH (1 ml) and 1.25M HCl in MeOH was added (0.1 ml). The mixture was dried to give a white solid (47 mg).

Workup

  1. concentrationThe crude product was concentrated
  2. custompurified on MDAP
  3. customThe product-containing fractions were evaporated to dryness
  4. washeluted with MeOH (15 ml) and 2M methanolic ammonia (15 ml)
  5. customThe basic fractions were evaporated
  6. customto give a white solid which
  7. customThe mixture was dried

Sources & evidence

ORD record
ord-2270e36dfc0049289eacbaabb3f9ac91
Source dataset
uspto-grants-2014_04
Patent number
US08697725B2

Reaction notes

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