Diisopropylethylamine → HCID 68431691, compound

HRID 2246247Notes

Reaction equation

HRID 2246247 reaction equation
[C:1]([C:5]([NH:7][C@@H:8]([C@@H:12]([C:14]1[O:18][N:17]=[C:16]([C:19]2[CH:24]=[CH:23][C:22]([S:25]([CH3:28])(=[O:27])=[O:26])=[CH:21][C:20]=2[Cl:29])[N:15]=1)[CH3:13])[C:9](O)=[O:10])=[O:6])([CH3:4])([CH3:3])[CH3:2].[NH:30]1[CH2:37][CH2:36][CH2:35][C@H:31]1[C:32]([NH2:34])=[O:33].C1C=NC2N(O)N=NC=2C=1.C(N(CC)C(C)C)(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>ClCCl>[C:1]([C:5]([NH:7][C@@H:8]([C@@H:12]([C:14]1[O:18][N:17]=[C:16]([C:19]2[CH:24]=[CH:23][C:22]([S:25]([CH3:28])(=[O:27])=[O:26])=[CH:21][C:20]=2[Cl:29])[N:15]=1)[CH3:13])[C:9]([N:30]1[CH2:37][CH2:36][CH2:35][C@H:31]1[C:32]([NH2:34])=[O:33])=[O:10])=[O:6])([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 5

HCID 81531DiisopropylethylamineHCID 111306L-ProlinamideHCID 181649HOAtHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 68431243HCID 68431243, compound

Product 1

HCID 68431691HCID 68431691, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To the crude acid from Step D (0.15 g, 0.33 mmol) in 5 mL of dichloromethane was added L-prolineamide (0.057 g, 0.49 mmol), HOAt (0.090 g, 0.66 mmol), N,N-diisopropylethylamine (0.17 mL, 0.99 mmol) and HATU (0.25 g, 0.66 mmol). After stirring at room temperature for 12 h, the reaction was diluted with dichloromethane. The organic phase was washed sequentially with two portions of 0.5N aqueous sodium bicarbonate solution and saturated aqueous brine, dried over sodium sulfate, and evaporated in vacuo. Purification by HPLC (YMC Pro-C18 column, gradient elution, 10-90% acetonitrile/water with 0.1% TFA) afforded the title compound. LC/MS 556.2 (M+1).

Workup

  1. washThe organic phase was washed sequentially with two portions of 0.5N aqueous sodium bicarbonate solution and saturated aqueous brine
  2. dry with materialdried over sodium sulfate
  3. customevaporated in vacuo
  4. customPurification
  5. washby HPLC (YMC Pro-C18 column, gradient elution, 10-90% acetonitrile/water with 0.1% TFA)

Sources & evidence

ORD record
ord-380753544bc14a1399be65ae667ec52b
Source dataset
uspto-grants-2010_03
Patent number
US07687492B2

Reaction notes

Loading…