Diisopropylethylamine → 1-Hydroxybenzotriazole

HRID 1062331Notes

Reaction equation

HRID 1062331 reaction equation
[CH2:1]1[CH2:5][N:4]([P+:6]([O:17][N:18]2[N:26]=[N:25][C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][C:19]2=3)([N:12]2[CH2:16][CH2:15][CH2:14][CH2:13]2)[N:7]2[CH2:11][CH2:10][CH2:9][CH2:8]2)[CH2:3][CH2:2]1.[F:27][P-:28]([F:33])([F:32])([F:31])([F:30])[F:29].[CH:34]1[CH:35]=[CH:36][C:37]2[N:42]([OH:43])[N:41]=[N:40][C:38]=2[CH:39]=1.CCN(C(C)C)C(C)C>CN(C=O)C.C(Cl)Cl>[CH2:1]1[CH2:5][N:4]([P+:6]([O:17][N:18]2[N:26]=[N:25][C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][C:19]2=3)([N:7]2[CH2:11][CH2:10][CH2:9][CH2:8]2)[N:12]2[CH2:13][CH2:14][CH2:15][CH2:16]2)[CH2:3][CH2:2]1.[F:27][P-:28]([F:33])([F:32])([F:31])([F:30])[F:29].[CH:34]1[CH:35]=[CH:36][C:37]2[N:42]([OH:43])[N:41]=[N:40][C:38]=2[CH:39]=1

Participants

6

Reactant 2

HCID 81531DiisopropylethylamineHCID 86598650HCID 86598650, compound

Product 2

HCID 757711-HydroxybenzotriazoleHCID 2724699PyBOP

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 6344DichloromethaneSolvent

Procedure

Solutions of each acid (RN) were prepared (1.08 mmol) in DMF (3 mL) (enough for 6 cartridges per acid). Solutions of PyBOP (3.74 g, 7.2 mmol) and HOBT (0.96 g, 7.2 mmol) in DMF (24 mL) were prepared. To each cartridge on a Bohdan block was added acid solution (0.5 niL, 0.18 mmol) according to product layout (6 cartridges of each of the 8 acids). To each cartridge was added the PyBOP/HOBT solution (0.5 mL, 0.078 g PYBOP, 0.15 mmol/0.02g HOBT, 0.15 mmol) and DIEA (0.052 mL, 0.30 mmol). The Bohdan block was agitated on a Bohdan shaker at 700-800 rpm for 1 h. A solution of amine was prepared (2.30 g, 7.2 mmol) in 24 mL of CH2Cl2. To each cartridge was added 0.5 mL of amine solution (0.48 g, 0.15 mmol). The Bohdan block was agitated on the Bohdan shaker at 700-800 rpm for 16 h. The reaction mixtures were drained into 48 well Robbin's blocks. Each cartridge was rinsed with 0.5 mL DMF into another 48 well Robbin's block. The reaction mixtures were concentrated in the Robbin's blocks under reduced pressure at 50° C. for 6 h in a Jouan centrifugal evaporator. Products were carried on crude to next reaction.

Workup

  1. additionTo each cartridge on a Bohdan block was added acid solution (0.5 niL, 0.18 mmol)
  2. stirringThe Bohdan block was agitated on the Bohdan shaker at 700-800 rpm for 16 h
  3. customThe reaction mixtures
  4. washEach cartridge was rinsed with 0.5 mL DMF into another 48 well Robbin's block
  5. customThe reaction mixtures
  6. concentrationwere concentrated in the Robbin's blocks under reduced pressure at 50° C. for 6 h in a Jouan centrifugal evaporator
  7. customProducts were carried on crude to next reaction

Sources & evidence

ORD record
ord-a92f63efb7664e0182c02ccbcae911ff
Source dataset
uspto-grants-2005_11
Patent number
US06960664B2

Reaction notes

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