Triethylamine → HCID 46909016, compound

HRID 1925543Notes

Reaction equation

HRID 1925543 reaction equation
CCN(CC)CC.[F:8][C:9]([F:30])([F:29])[C:10]1[CH:11]=[C:12]([CH2:16][CH2:17][CH2:18][CH2:19][C:20]2[N:28]=[CH:27][CH:26]=[CH:25][C:21]=2[C:22]([OH:24])=O)[CH:13]=[CH:14][CH:15]=1.[NH2:31][CH2:32][C:33]1[S:34][CH:35]=[CH:36][CH:37]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>C1COCC1>[S:34]1[CH:35]=[CH:36][CH:37]=[C:33]1[CH2:32][NH:31][C:22]([C:21]1[C:20]([CH2:19][CH2:18][CH2:17][CH2:16][C:12]2[CH:13]=[CH:14][CH:15]=[C:10]([C:9]([F:8])([F:30])[F:29])[CH:11]=2)=[N:28][CH:27]=[CH:26][CH:25]=1)=[O:24]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 34005(2-Thienylmethyl)amineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 67133908HCID 67133908, compound

Product 1

HCID 46909016HCID 46909016, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

NEt3 was added to a solution of 323 mg (1.0 mmol) of 2-(4-(3-trifluoromethyl-phenyl)butyl)nicotinic acid (VB005), 113 mg (1.0 mmol) of 2-(aminomethyl)-thiophene and 381 mg (1.0 mmol) of HATU in THF (8 ml) and stirring was carried out for 4 d at RT. The mixture was then concentrated in vacuo. The residue was taken up in EA and washed with a 1M aq. NH4Cl sol. and a 1M aq. NaHCO3 sol. The organic phase was dried over MgSO4, filtered and concentrated in vacuo. The residue was purified by means of CC (EA/hex 3:1), yielding 221 mg (0.5 mmol, 53%). MS: m/z 419.1 [M+H]+.

Workup

  1. concentrationThe mixture was then concentrated in vacuo
  2. washwashed with a 1M aq. NH4Cl sol.
  3. dry with materiala 1M aq. NaHCO3 sol. The organic phase was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by means of CC (EA/hex 3:1)
  7. customyielding 221 mg (0.5 mmol, 53%)

Sources & evidence

ORD record
ord-21f059deed734aa8bf02ac675449538a
Source dataset
uspto-grants-2012_05
Patent number
US08178684B2

Reaction notes

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