Pyrrolidine → HCID 59845673, compound

HRID 1819457Notes

Reaction equation

HRID 1819457 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]1[CH2:14][CH2:13][CH:12]([CH2:15][NH:16][C:17]2[C:22]([N+:23]([O-:25])=[O:24])=[CH:21][N:20]=[C:19]([NH:26][CH2:27][C:28]([OH:30])=O)[N:18]=2)[CH2:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH:31]1[CH2:35][CH2:34][CH2:33][CH2:32]1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C(N(C(C)C)CC)(C)C>CN(C=O)C.C(OCC)(=O)C>[C:1]([O:5][C:6](=[O:7])[NH:8][CH:9]1[CH2:14][CH2:13][CH:12]([CH2:15][NH:16][C:17]2[C:22]([N+:23]([O-:25])=[O:24])=[CH:21][N:20]=[C:19]([NH:26][CH2:27][C:28](=[O:30])[N:31]3[CH2:35][CH2:34][CH2:33][CH2:32]3)[N:18]=2)[CH2:11][CH2:10]1)([CH3:3])([CH3:4])[CH3:2]

Participants

7

Reactant 4

HCID 31268PyrrolidineHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 59845662HCID 59845662, compound

Product 1

HCID 59845673HCID 59845673, compoundYield 14.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To {4-[(4-tert-butoxycarbonylamino-cyclohexylmethyl)-amino]-5-nitro-pyrimidin-2-ylamino}-acetic acid (120 mg, 0.28 mmol) in DMF (1.5 mL) were added pyrrolidine (48 μL, 0.57 mmol), TBTU (141 mg, 0.43 mmol), and diisopropylethylamine (99 μL, 0.57 mmol). The reaction mixture was stirred at room temperature for 16 h. The mixture was diluted with ethyl acetate and washed with water (×2) and brine. The organic phase was dried over Na2SO4 and concentrated. The resulting residue was purified by silica gel prep TLC using 95:5 CH2Cl2:MeOH as an eluant to afford 19 mg of (4-{[5-nitro-2-(2-oxo-2-pyrrolidin-1-yl-ethylamino)-pyrimidin-4-ylamino]-methyl}-cyclohexyl)-carbamic acid tert-butyl ester as a light brown solid.

Workup

  1. washwashed with water (×2) and brine
  2. dry with materialThe organic phase was dried over Na2SO4
  3. concentrationconcentrated
  4. customThe resulting residue was purified by silica gel prep TLC

Sources & evidence

ORD record
ord-91f044ac233c4c6a86a646f20d5bbd0b
Source dataset
uspto-grants-2009_10
Patent number
US07601714B2

Reaction notes

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