Triethylamine → HCID 86605054, compound

HRID 1394928Notes

Reaction equation

HRID 1394928 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[C:9]1[CH2:13][N:12]([C:14]([N:16]2[CH:20]=C[N+](C)=C2)=[O:15])[C@H:11]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:10]=1.NC1[CH2:34][CH2:33][N:32]([C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])[CH2:31][CH2:30]1.CCN(CC)CC>C(Cl)Cl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[C:9]1[CH2:13][N:12]([C:14]([NH:16][CH:20]2[CH2:34][CH2:33][N:32]([C:35]([O:37][C:38]([CH3:40])([CH3:39])[CH3:41])=[O:36])[CH2:31][CH2:30]2)=[O:15])[C@H:11]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:10]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 12682914-Amino-1-Boc-piperidineHCID 59682327HCID 59682327, compound

Product 1

HCID 86605054HCID 86605054, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Crude 18-2 (115 mg, 0.24 mmol) was suspended in anhydrous CH2CL2 (3 mL) and treated successively with 4-amino-1-tert-butyloxycarbonyl-piperidine (235 mg, 1.17 mmol) and Et3N (0.1 mL, 0.7 mmol). The suspension was stirred for 6 hours and complete dissolution was observed. Upon completion, the reaction was diluted further with CH2Cl2 (20 mL) and washed with 1N HCl to remove all unbound amine and Et3N. The organic layer was dried (MgSO4), filtered and concentrated under reduced pressure to yield crude 18-3 as a yellow oil: LRMS m/z (N C(CH3)3+H) 427.9 found, 428.1 required.

Workup

  1. dissolutioncomplete dissolution
  2. washwashed with 1N HCl
  3. customto remove all unbound amine and Et3N
  4. dry with materialThe organic layer was dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-9d670c402433424d85712068ca9111ae
Source dataset
uspto-grants-2008_03
Patent number
US07348440B2

Reaction notes

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