Diisopropylethylamine → HCID 45274207, compound

HRID 1667092Notes

Reaction equation

HRID 1667092 reaction equation
[O:1]=[C:2]1[C:6]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH2:5][CH2:4][N:3]1[CH2:19][C:20](O)=[O:21].[CH:23]([N:36]1[CH2:41][CH2:40][NH:39][CH2:38][C:37]1=[O:42])([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.C(N(C(C)C)CC)(C)C>C(Cl)Cl>[CH:23]([N:36]1[CH2:41][CH2:40][N:39]([C:20](=[O:21])[CH2:19][N:3]2[CH2:4][CH2:5][C:6]([C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=3)([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:2]2=[O:1])[CH2:38][C:37]1=[O:42])([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 67358523HCID 67358523, compoundHCID 673590132-(2-Oxo-3,3-diphenylpyrrolidin-1-yl)acetic acid

Product 1

HCID 45274207HCID 45274207, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 2-(2-oxo-3,3-diphenylpyrrolidin-1-yl)acetic acid (Example 1C, 0.18 g, 0.6 mmol) and the product from Example 28A (0.18 g, 0.6 mmol) in methylene chloride (10 mL) was added O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (0.23 g, 0.6 mmol) and diisopropylethylamine (0.5 mL). The reaction mixture was stirred at ambient temperature overnight. The reaction mixture was then diluted with methylene chloride, and then washed with 1 N HCl, water, 1 N NaOH, and water. The organic layer was dried over magnesium sulfate and concentrated in vacuo to yield the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 7.28 (m, 20H), 6.91 (s, 1H), 4.26 (d, J=21.70 Hz, 2H), 4.18 (d, J=12.88 Hz, 2H), 3.69 (m, 2H), 3.35 (m, 2H), 3.13 (m, 1H), 3.07 (m, 1H), 2.71 (m, 2H), 2.69 (s, 1H); MS (ESI+) m/z 544 (M+H)+.

Workup

  1. washwashed with 1 N HCl, water, 1 N NaOH, and water
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-be5af9b149ae4974ae4994b77ce1e2e7
Source dataset
uspto-grants-2011_10
Patent number
US08044069B2

Reaction notes

Loading…