1-Hydroxybenzotriazole → HCID 18621190, compound

HRID 1861985Notes

Reaction equation

HRID 1861985 reaction equation
Cl.[C:2]([C:4]1[CH:9]=[CH:8][C:7]([CH:10]2[CH2:14][S:13][C:12]3=[N:15][CH:16]=[C:17]([C:18]([OH:20])=O)[N:11]23)=[CH:6][C:5]=1F)#[N:3].[Br:22][C:23]1[CH:36]=[CH:35][C:34]([O:37][Si:38]([C:51]([CH3:54])([CH3:53])[CH3:52])([C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=2)[C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)=[CH:33][C:24]=1[CH2:25][N:26]1[CH2:31][CH2:30][NH:29][CH2:28][C:27]1=[O:32].CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1.C(N(CC)C(C)C)(C)C>>[Br:22][C:23]1[CH:36]=[CH:35][C:34]([O:37][Si:38]([C:51]([CH3:54])([CH3:53])[CH3:52])([C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=2)=[CH:33][C:24]=1[CH2:25][N:26]1[CH2:31][CH2:30][N:29]([C:18]([C:17]2[N:11]3[C:12]([S:13][CH2:14][CH:10]3[C:7]3[CH:6]=[CH:5][C:4]([C:2]#[N:3])=[CH:9][CH:8]=3)=[N:15][CH:16]=2)=[O:20])[CH2:28][C:27]1=[O:32]

Participants

6

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 18621214HCID 18621214, compoundHCID 69933649HCID 69933649, compound

Product 1

HCID 18621190HCID 18621190, compound

Procedure

The carboxylic acid from Step K (221 mg, 0.679 mmol), the piperazinone from Step E (390 mg, 0.679 mmol), EDC hydrochloride (156 mg, 0.814 mmol), HOBT (110 mg, 0.814 mmol), and N,N-diisopropylethylamine (0.591 mL, 3.39 mmol) were stirred together in dry, degassed DMF (5 mL) at 25° C. for 16 hours. The reaction was poured onto saturated aqueous sodium bicarbonate and extracted with methylene chloride (3×25 mL). The combined organic layers were washed with brine, dried over sodium sulfate, filtered, and concentrated in vacuo to provide a yellow oil. The crude product was purified by column chromatography (3% methanol/methylene chloride) to provide the title compound as a yellow solid.

Workup

  1. customin dry
  2. customdegassed DMF (5 mL) at 25° C. for 16 hours
  3. additionThe reaction was poured onto saturated aqueous sodium bicarbonate
  4. extractionextracted with methylene chloride (3×25 mL)
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customto provide a yellow oil
  10. customThe crude product was purified by column chromatography (3% methanol/methylene chloride)

Sources & evidence

ORD record
ord-316b452015ef4eed880d29447ef0c7b7
Source dataset
uspto-grants-2003_03
Patent number
US06534506B2

Reaction notes

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