1-Methylimidazole → HCID 86706369, compound

HRID 1396931Notes

Reaction equation

HRID 1396931 reaction equation
CN1C=CN=C1.[CH:7]1([CH2:12][C@H:13]([CH2:34][N:35]([CH:44]=[O:45])[O:36][CH2:37][C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[C:14]([N:16]2[C@H:20]([C:21]([OH:23])=O)[CH2:19][CH2:18][N:17]2[C:24]([O:26][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[O:25])=[O:15])[CH2:11][CH2:10][CH2:9][CH2:8]1.S(Cl)(C)(=O)=O.[CH3:51][N:52]([CH2:54][C:55]1[N:60]=[C:59]([NH2:61])[CH:58]=[CH:57][N:56]=1)[CH3:53]>C(Cl)Cl>[CH:7]1([CH2:12][C@H:13]([CH2:34][N:35]([CH:44]=[O:45])[O:36][CH2:37][C:38]2[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=2)[C:14]([N:16]2[C@H:20]([C:21]([NH:61][C:59]3[CH:58]=[CH:57][N:56]=[C:55]([CH2:54][N:52]([CH3:53])[CH3:51])[N:60]=3)=[O:23])[CH2:19][CH2:18][N:17]2[C:24]([O:26][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[O:25])=[O:15])[CH2:8][CH2:9][CH2:10][CH2:11]1

Participants

6

Reactant 4

HCID 13901-MethylimidazoleHCID 31297Methanesulfonyl chlorideHCID 68287771HCID 68287771, compoundHCID 86706346(3S)-2-[(2R)-3-cyclopentyl-2-({formyl[(phenylmethyl)oxy]amino}methyl)propanoyl]-1-{[(phenylmethyl)oxy]carbonyl}-3-pyrazolidinecarboxylic acid

Product 1

HCID 86706369HCID 86706369, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

1-Methylimidazole (178 μl, 2.232 mmol) was added into the solution of (3S)-2-[(2R)-3-cyclopentyl-2-({formyl[(phenylmethyl)oxy]amino}methyl)propanoyl]-1-{[(phenylmethyl)oxy]carbonyl}-3-pyrazolidinecarboxylic acid (400 mg, 0.744 mmol) in DCM (4.08 ml). The resulting solution was cooled to 0° C., and then mesyl chloride (60.5 μl, 0.781 mmol) was added dropwise at 0° C. To the reaction mixture was added 2-[(dimethylamino)methyl]-4-pyrimidinamine (147 mg, 0.967 mmol) in 1 ml of DCM. After stirring for 1.5 hrs at ambient temperature, the solvent was removed under reduced pressure to give a residue which was purified by RP-HPLC to yield phenylmethyl (3S)-2-[(2R)-3-cyclopentyl-2-({formyl[(phenylmethyl)oxy]amino}methyl)propanoyl]-3[({2-[(dimethylamino) methyl]-4-pyrimidinyl}amino)carbonyl]-1-pyrazolidine carboxylate (104 mg, 0.147 mmol, 20% yield). MS (ES+) m/z 672.2 (MH+).

Workup

  1. customthe solvent was removed under reduced pressure
  2. customto give a residue which
  3. customwas purified by RP-HPLC

Sources & evidence

ORD record
ord-c375e16d272e466aa7c84c0b44c7f2d9
Source dataset
uspto-grants-2014_12
Patent number
US08901119B2

Reaction notes

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