Water → HCID 24751376, compound

HRID 1713100Notes

Reaction equation

HRID 1713100 reaction equation
Cl.Cl.[CH3:3][C:4]1[N:9]=[N:8][C:7]([C:10]2[CH:11]=[C:12]3[C:17](=[CH:18][CH:19]=2)[CH2:16][N:15]([CH2:20][C:21]([OH:23])=O)[CH2:14][CH2:13]3)=[CH:6][CH:5]=1.F[P-](F)(F)(F)(F)F.[N:31]1(O[P+](N(C)C)(N(C)C)N(C)C)[C:35]2[CH:36]=[CH:37][CH:38]=CC=2N=N1.O>C(Cl)Cl>[CH:35]1([N:31]2[CH2:17][CH2:16][N:15]([C:21](=[O:23])[CH2:20][N:15]3[CH2:14][CH2:13][C:12]4[C:17](=[CH:18][CH:19]=[C:10]([C:7]5[N:8]=[N:9][C:4]([CH3:3])=[CH:5][CH:6]=5)[CH:11]=4)[CH2:16]3)[CH2:14][CH2:13]2)[CH2:36][CH2:37][CH2:38]1

Participants

5

Reactant 3

HCID 962WaterHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 66877716HCID 66877716, compound

Product 1

HCID 24751376HCID 24751376, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of [6-(6-methyl-pyridazin-3-yl)-3,4-dihydro-1H-isoquinolin-2-yl]-acetic acid dihydrochloride (313 mg, 0.88 mmol) and 1-cyclobutyl-piperazine bistrifluoroacetate (356 mg, 0.97 mmol, 1.1 eq.) in DCM (10.0 ml) are added BOP (467 mg, 1.06 mmol, 1.2 eq.) and TEA (267 mg, 2.64 mmol, 3.0 eq.). The mixture is stirred at rt for 2 hr. Water (10.0 ml) is added to quench the reaction, and the organic layer is collected, dried over sodium sulfate, and concentrated. The residue is purified by PTLC (EtOAc/4% TEA) to give the title compound. 1H NMR (300 MHz, CDCl3) δ 7.85 (1H, s), 7.78 (1H, dd), 7.72 (1H, d), 7.36 (1H, d), 7.15 (1H, d), 3.75 (2H, s), 3.65 (4H, m), 3.39 (2H, s), 2.99 (2H, t), 2.82 (2H, t), 2.74 (3H, s), 2.68 (1H, m), 2.28 (4H, m), 1.64-2.08 (6H, m); MS (+VE) m/z 406.2 (M++1).

Workup

  1. customto quench
  2. customthe reaction
  3. customthe organic layer is collected
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customThe residue is purified by PTLC (EtOAc/4% TEA)

Sources & evidence

ORD record
ord-0dbdae91d9684eccb80b557d15ca42b7
Source dataset
uspto-grants-2010_09
Patent number
US07795262B2

Reaction notes

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