1-Pyrrolidineethanamine → HCID 68777550, compound

HRID 2191091Notes

Reaction equation

HRID 2191091 reaction equation
F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.[NH2:28][CH2:29][CH2:30][N:31]1[CH2:35][CH2:34][CH2:33][CH2:32]1.[CH3:36][C:37]1([CH3:65])[CH2:63][C:41]2[C:42]([C:51]3[CH:52]=[C:53]([NH:57][C:58](=[O:62])[C:59](O)=[O:60])[CH:54]=[CH:55][CH:56]=3)=[C:43]([N:45]3[CH2:50][CH2:49][O:48][CH2:47][CH2:46]3)[S:44][C:40]=2[C:39](=[O:64])[CH2:38]1>C(Cl)Cl>[CH3:36][C:37]1([CH3:65])[CH2:63][C:41]2[C:42]([C:51]3[CH:52]=[C:53]([NH:57][C:58](=[O:62])[C:59]([NH:28][CH2:29][CH2:30][N:31]4[CH2:35][CH2:34][CH2:33][CH2:32]4)=[O:60])[CH:54]=[CH:55][CH:56]=3)=[C:43]([N:45]3[CH2:50][CH2:49][O:48][CH2:47][CH2:46]3)[S:44][C:40]=2[C:39](=[O:64])[CH2:38]1

Participants

5

Reactant 3

HCID 13441-Pyrrolidineethanamine2×HCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 68775846HCID 68775846, compound

Product 1

HCID 68777550HCID 68777550, compoundYield 19.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (145 mg, 0.33 mmol) and 1-(2-aminoethyl)pyrrolidine (60 μL, 0.49 mmol) were added to a solution of Example 292 (70 mg, 0.16 mmol) in DCM (10 mL) and the reaction mixture was stirred at room temperature for 18 h. A further portion of 1-(2-aminoethyl)-pyrrolidine (60 μL, 0.49 mmol) was added and stirring was continued for 72 h. The solvent was removed in vacuo and the residue was purified by preparative HPLC (pH 2.5) to give the title compound (16 mg, 19%) as an off-white solid. δH (CDCl3) 9.26 (1H, s), 8.43 (1H, br s), 7.74-7.69 (1H, m), 7.65-7.59 (1H, m), 7.45 (1H, t, J 7.7 Hz), 7.23-7.16 (1H, m), 3.78-3.64 (6H, m), 3.11-2.92 (10H, m), 2.49 (2H, s), 2.45 (2H, s), 2.07-1.96 (4H, m), 1.05 (6H, s). LCMS (ES+) 525.3 (M+H)+.

Workup

  1. stirringstirring
  2. waitwas continued for 72 h
  3. customThe solvent was removed in vacuo
  4. customthe residue was purified by preparative HPLC (pH 2.5)

Sources & evidence

ORD record
ord-c0cde4e1770e48578cc57be35ae0c346
Source dataset
uspto-grants-2012_12
Patent number
US08324204B2

Reaction notes

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