Triethylamine → HCID 46941029, compound

HRID 2354364Notes

Reaction equation

HRID 2354364 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.[Cl:28][C:29]1[CH:30]=[CH:31][C:32]2[O:36][C:35](=[O:37])[N:34]([CH2:38][C:39]([OH:41])=O)[C:33]=2[CH:42]=1.[C:43]1([C:59]2[CH:64]=[CH:63][CH:62]=[CH:61][CH:60]=2)[CH:48]=[CH:47][C:46]([C:49]([NH:57][CH3:58])([CH3:56])[CH2:50][N:51]2[CH2:55][CH2:54][CH2:53][CH2:52]2)=[CH:45][CH:44]=1.CCN(CC)CC>CN(C=O)C>[C:43]1([C:59]2[CH:60]=[CH:61][CH:62]=[CH:63][CH:64]=2)[CH:48]=[CH:47][C:46]([C:49]([N:57]([CH3:58])[C:39](=[O:41])[CH2:38][N:34]2[C:33]3[CH:42]=[C:29]([Cl:28])[CH:30]=[CH:31][C:32]=3[O:36][C:35]2=[O:37])([CH3:56])[CH2:50][N:51]2[CH2:55][CH2:54][CH2:53][CH2:52]2)=[CH:45][CH:44]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 3921330(5-CHLORO-2-OXO-BENZOOXAZOL-3-YL)-ACETIC ACIDHCID 57425539HCID 57425539, compound

Product 1

HCID 46941029HCID 46941029, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

BOP (133 mg, 0.30 mmol) was added to a mixture containing (5-chloro-2-oxo-1,3-benzoxazol-3(2H)-yl)acetic acid (68 mg, 0.30 mmol), 2-(4-biphenylyl)-N-methyl-1-(1-pyrrolidinyl)-2-propanamine (74 mg, 0.25 mmol) and Et3N (0.042 ml, 0.30 mmol) in DMF (3 ml) and the resulting mixture was stirred at room temperature for 16 h. The crude reaction mixture was purified by preparative HPLC (Xterra PrepRP 30×100 mm, 45 mL/min, A: acetonitrile B: water, PH 10, A: 50 to 90% over 12 min, UV detection at 214 nm) to give 17.5 mg (13.9%) as a white solid. MS (ES) m/e 504.4 [M+H]+.

Workup

  1. customThe crude reaction mixture
  2. customwas purified by preparative HPLC (Xterra PrepRP 30×100 mm, 45 mL/min
  3. waitA: acetonitrile B: water, PH 10, A: 50 to 90% over 12 min
  4. customUV detection at 214 nm) to give 17.5 mg (13.9%) as a white solid

Sources & evidence

ORD record
ord-3afe8813d29046a0899afd960a895139
Source dataset
uspto-grants-2010_07
Patent number
US07749998B2

Reaction notes

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