Pyrrolidine → HCID 68622093, compound

HRID 1244687Notes

Reaction equation

HRID 1244687 reaction equation
C([N:3]([CH:7]([CH3:9])C)[CH:4]([CH3:6])C)C.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.[C:34]([O:38][C:39]([NH:41][CH:42]1[CH:59]([C:60]([OH:62])=O)[CH2:58][N:45]2[CH2:46][CH2:47][C:48]3[C:53]([CH:44]2[CH2:43]1)=[CH:52][C:51]([O:54][CH3:55])=[C:50]([O:56][CH3:57])[CH:49]=3)=[O:40])([CH3:37])([CH3:36])[CH3:35].N1CCCC1>CN(C=O)C>[C:34]([O:38][C:39](=[O:40])[NH:41][CH:42]1[CH:59]([C:60]([N:3]2[CH2:4][CH2:6][CH2:9][CH2:7]2)=[O:62])[CH2:58][N:45]2[CH2:46][CH2:47][C:48]3[C:53]([CH:44]2[CH2:43]1)=[CH:52][C:51]([O:54][CH3:55])=[C:50]([O:56][CH3:57])[CH:49]=3)([CH3:37])([CH3:36])[CH3:35]

Participants

6

Reactant 4

HCID 31268PyrrolidineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 21919474HCID 21919474, compound

Product 1

HCID 68622093HCID 68622093, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N-Ethyldiisopropylamine (96 mg, 0.74 mmol) and O-(7-Azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (HATU, 103 mg, 0.27 mmol) were added at r.t. to a suspension of (RS,RS,RS)-2-tert-butoxycarbonylamino-9,10-dimethoxy-1,3,4,6,7,11b-hexahydro-2H-pyrido[2,1-a]isoquinoline-3-carboxylic acid (100 mg, 0.25 mmol) in N,N,dimethylformamide (2 mL), then after 45 min pyrrolidine (19 mg, 0.27 mmol) was added. The homogeneous solution was stirred 90 min at r.t., then partitioned between hexane/ethyl acetate 1:1 and water. The organic layer was washed with brine, dried (MgSO4), and evaporated, and the residue chromatographed (SiO2, CH2Cl2/MeOH/NH4OH 80:1:0.2) to produce the title compound (58 mg, 51%). Light yellow solid, MS (ISP) 460.5 (M+H)+.

Workup

  1. custompartitioned between hexane/ethyl acetate 1:1 and water
  2. washThe organic layer was washed with brine
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. customthe residue chromatographed (SiO2, CH2Cl2/MeOH/NH4OH 80:1:0.2)

Sources & evidence

ORD record
ord-91541ecf82294c18b1a0fd76311f924d
Source dataset
uspto-grants-2006_10
Patent number
US07122555B2

Reaction notes

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