Ammonium Chloride → HCID 86595609, compound

HRID 2117942Notes

Reaction equation

HRID 2117942 reaction equation
[C:1]([O:5][C:6](=[O:27])[NH:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][C:16]2[N:17]=[C:18]([NH:23][C:24](=[O:26])[CH3:25])[S:19][C:20]=2[CH:21]=O)=[CH:10][CH:9]=1)([CH3:4])([CH3:3])[CH3:2].Cl.[CH3:29][N:30]([CH3:38])[C:31]([C@@H:33]1[CH2:37][CH2:36][CH2:35][NH:34]1)=[O:32].C(N(C(C)C)CC)(C)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[NH4+].[Cl-]>ClCCl>[C:1]([O:5][C:6](=[O:27])[NH:7][C:8]1[CH:9]=[CH:10][C:11]([CH2:14][CH2:15][C:16]2[N:17]=[C:18]([NH:23][C:24](=[O:26])[CH3:25])[S:19][C:20]=2[CH2:21][N:34]2[CH2:35][CH2:36][CH2:37][C@H:33]2[C:31]([N:30]([CH3:38])[CH3:29])=[O:32])=[CH:12][CH:13]=1)([CH3:3])([CH3:4])[CH3:2]

Participants

7

Reactant 5

HCID 25517Ammonium ChlorideHCID 81531DiisopropylethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 21914852HCID 21914852, compoundHCID 66702040(S)-N,N-DiMethyl-2-pyrrolidinecarboxaMide HCl

Product 1

HCID 86595609HCID 86595609, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
5 °C

Procedure

To a solution of the compound obtained in Step 2 (200 mg) in dichloromethane (6 mL) were added (2S)-2-(N,N-dimethylaminocarbonyl)pyrrolidine hydrochloride and diisopropylethylamine (0.27 ml) at 5° C. The mixture was stirred at 5° C. for 10 min. Then sodium triacetoxyborohydride (327 mg) was added, and the mixture was stirred for 3 hrs. aq. NH4Cl was added, and the mixture was extracted with dichloromethane. The organic layer was dried over MgSO4. The layer was concentrated under reduced pressure. The resulting crude mixture was purified by silica gel column chlomatography with mixed solvent (dichloromethane/methanol=15/1) as an eluent to give tert-butyl(4-{2-[2-(acetylamino)-5-({(2S)-2-[(N,N-dimethylamino)carbonyl]-1-pyrrolidinyl}methyl)-1,3-thiazol-4-yl]ethyl}phenyl)carbamate as a pale yellow amorphous substance.

Workup

  1. stirringthe mixture was stirred for 3 hrs
  2. extractionthe mixture was extracted with dichloromethane
  3. dry with materialThe organic layer was dried over MgSO4
  4. concentrationThe layer was concentrated under reduced pressure
  5. customThe resulting crude mixture was purified by silica gel column chlomatography with mixed solvent (dichloromethane/methanol=15/1) as an eluent

Sources & evidence

ORD record
ord-b0901af53eeb4d9882e9ca01c9fa23d5
Source dataset
uspto-grants-2008_10
Patent number
US07442715B2

Reaction notes

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