Triethylamine → HCID 25164161, compound

HRID 1913804Notes

Reaction equation

HRID 1913804 reaction equation
[O:1]1[CH2:5][CH2:4][CH2:3][C@H:2]1[CH2:6][O:7][C:8]1[CH:16]=[CH:15][C:11]([C:12]([OH:14])=O)=[CH:10][CH:9]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C.[N:48]1([CH2:53][C:54]2[CH:55]=[C:56]3[C:61](=[CH:62][CH:63]=2)[CH2:60][C@@H:59]([NH2:64])[CH2:58][CH2:57]3)[CH2:52][CH2:51][CH2:50][CH2:49]1>CN1C(=O)CCC1.C(OCC)(=O)C>[N:48]1([CH2:53][C:54]2[CH:55]=[C:56]3[C:61](=[CH:62][CH:63]=2)[CH2:60][C@@H:59]([NH:64][C:12](=[O:14])[C:11]2[CH:10]=[CH:9][C:8]([O:7][CH2:6][C@@H:2]4[CH2:3][CH2:4][CH2:5][O:1]4)=[CH:16][CH:15]=2)[CH2:58][CH2:57]3)[CH2:52][CH2:51][CH2:50][CH2:49]1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 2402152HCID 2402152, compoundHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 66663464(S)-6-Pyrrolidin-1-ylmethyl-1,2,3,4-tetrahydronaphthalen-2-ylamine

Product 1

HCID 25164161HCID 25164161, compound

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 13387N-methyl-2-pyrrolidoneSolvent2×

Procedure

To a solution of 4-[(S)-1-(TETRAHYDROFURAN-2-YL)METHOXY]BENZOIC ACID (3.38 g) in NMP (30 ml) were added HATU (O-(7-AZABENZOTRIAZOL-1-YL)-N,N,N′,N′-TETRAMETHYLURONIUM HEXAFLUOROPHOSPHATE; 5.78 g) and then triethylamine (2.12 ml). A solution of (S)-6-pyrrolidin-1-ylmethyl-1,2,3,4-tetrahydronaphthalen-2-ylamine (3.5 g) in NMP (20 ml) was added dropwise. After 12 hours, the reaction mixture was diluted with ethyl acetate, washed with saturated sodium carbonate solution and concentrated. The residue was purified by chromatography on silica gel (eluent: 10:1 DCM/MeOH). The product was thus obtained with the molecular weight of 434.58 (C27H34N2O3); MS (ESI): 435 (M+H+).

Workup

  1. washwashed with saturated sodium carbonate solution
  2. concentrationconcentrated
  3. customThe residue was purified by chromatography on silica gel (eluent: 10:1 DCM/MeOH)
  4. customThe product was thus obtained with the molecular weight of 434.58 (C27H34N2O3)

Sources & evidence

ORD record
ord-3eb1a7ed7cef47fa9c1a82b7b39355d0
Source dataset
uspto-grants-2013_12
Patent number
US08609731B2

Reaction notes

Loading…