(2-Thienylmethyl)amine → HCID 46908823, compound

HRID 1925541Notes

Reaction equation

HRID 1925541 reaction equation
C1N=CN(C(N2C=NC=C2)=O)C=1.[F:13][C:14]([F:35])([F:34])[C:15]1[CH:16]=[C:17]([S:21][CH2:22][CH2:23][CH2:24][C:25]2[N:33]=[CH:32][CH:31]=[CH:30][C:26]=2[C:27]([OH:29])=O)[CH:18]=[CH:19][CH:20]=1.[NH2:36][CH2:37][C:38]1[S:39][CH:40]=[CH:41][CH:42]=1>C(Cl)Cl>[S:39]1[CH:40]=[CH:41][CH:42]=[C:38]1[CH2:37][NH:36][C:27]([C:26]1[C:25]([CH2:24][CH2:23][CH2:22][S:21][C:17]2[CH:18]=[CH:19][CH:20]=[C:15]([C:14]([F:13])([F:35])[F:34])[CH:16]=2)=[N:33][CH:32]=[CH:31][CH:30]=1)=[O:29]

Participants

5

Reactant 3

HCID 34005(2-Thienylmethyl)amineHCID 682631,1'-CarbonyldiimidazoleHCID 67134350HCID 67134350, compound

Product 1

HCID 46908823HCID 46908823, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

91 mg (0.6 mmol) of CDI were added to a solution of 240 mg (0.7 mmol) of 2-(3-(3-(trifluoromethyl)phenylthio)propyl)nicotinic acid (VB004) in DCM (7 ml), and stirring was carried out for 30 min at RT. 79 mg (0.7 mmol) of 2-(aminomethyl)thiophene were then added and stirring was carried out for a further 5 d at RT. The mixture was then washed with a 4M aq. NH4Cl sol. (2×10 ml) and a 1M NaHCO3 sol. (2×10 ml). The organic phase was dried over MgSO4, filtered and concentrated in vacuo. The residue was purified by means of CC (EA), yielding 134 mg (0.3 mmol, 44%). MS: m/z 437.1 [m+H]+.

Workup

  1. stirringstirring
  2. waitwas carried out for a further 5 d at RT
  3. washThe mixture was then washed with a 4M aq. NH4Cl sol. (2×10 ml)
  4. dry with materialThe organic phase was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by means of CC (EA)
  8. customyielding 134 mg (0.3 mmol, 44%)

Sources & evidence

ORD record
ord-b29920a65eb747f6af2c908855120fb6
Source dataset
uspto-grants-2012_05
Patent number
US08178684B2

Reaction notes

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