Ammonium Chloride → HCID 67196668, compound

HRID 2366897Notes

Reaction equation

HRID 2366897 reaction equation
[CH3:1][CH:2]([O:4][C:5](=[O:29])[NH:6][C@H:7]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([C:17]3[CH:22]=[CH:21][C:20]([CH:23]=O)=[CH:19][CH:18]=3)[CH:15]=2)[N:10]([C:25](=[O:27])[CH3:26])[C@@H:9]([CH3:28])[CH2:8]1)[CH3:3].[NH2:30][CH:31]1[CH2:36][CH2:35][N:34]([C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])[CH2:33][CH2:32]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[NH4+].[Cl-]>ClCCl.O>[C:25]([N:10]1[C:11]2[C:16](=[CH:15][C:14]([C:17]3[CH:22]=[CH:21][C:20]([CH2:23][NH:30][CH:31]4[CH2:32][CH2:33][N:34]([C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])[CH2:35][CH2:36]4)=[CH:19][CH:18]=3)=[CH:13][CH:12]=2)[C@H:7]([NH:6][C:5]([O:4][CH:2]([CH3:3])[CH3:1])=[O:29])[CH2:8][C@@H:9]1[CH3:28])(=[O:27])[CH3:26]

Participants

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 12682914-Amino-1-Boc-piperidineHCID 5049666Sodium triacetoxyborohydrideHCID 86669228HCID 86669228, compound

Product 1

HCID 67196668HCID 67196668, compoundYield 79%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 1-methylethyl[(2S,4R)-1-acetyl-6-(4-formylphenyl)-2-methyl-1,2,3,4-tetrahydro-4-quinolinyl]carbamate (for a preparation see intermediate 36) (500 mg, 1.268 mmol) and 1,1-dimethylethyl 4-amino-1-piperidinecarboxylate (400 mg, 1.997 mmol) in dichloromethane (DCM) (15 ml) was stirred 45 min at room temperature under nitrogen before being treated portionwise with sodium triacetoxyborohydride (457 mg, 2.155 mmol). The resulting mixture was stirred at room temperature for 20 h then treated with a saturated NH4Cl aqueous solution (8 mL) and diluted with water (10 mL). The layers were separated and the aqueous phase was washed with DCM (2×10 mL). The combined organic layers were dried over Na2SO4 then concentrated in vacuo. Purification of the residue by flash chromatography on silica gel (gradient: 1 to 10% MeOH in DCM) gave 1,1-dimethylethyl 4-[({4-[(2S,4R)-1-acetyl-2-methyl-4-({[(1-methylethyl)oxy]carbonyl}amino)-1,2,3,4-tetrahydro-6-quinolinyl]phenyl}methyl)amino]-1-piperidinecarboxylate (608 mg, 0.998 mmol, 79%) as a cream solid.

Workup

  1. stirringThe resulting mixture was stirred at room temperature for 20 h
  2. customThe layers were separated
  3. washthe aqueous phase was washed with DCM (2×10 mL)
  4. dry with materialThe combined organic layers were dried over Na2SO4
  5. concentrationthen concentrated in vacuo
  6. customPurification of the residue by flash chromatography on silica gel (gradient: 1 to 10% MeOH in DCM)

Sources & evidence

ORD record
ord-0e744d817d1c4e5c8dd95af3b491adb4
Source dataset
uspto-grants-2014_04
Patent number
US08697725B2

Reaction notes

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