1-Hydroxybenzotriazole → HCID 59393690, compound

HRID 2092130Notes

Reaction equation

HRID 2092130 reaction equation
[OH:1][N:2]=[C:3]([C:5]1[CH:6]=[N:7][C:8]([C:11]([C:16]2[CH:21]=[CH:20][C:19]([C:22]3[CH:23]=[N:24][CH:25]=[C:26]([O:28][CH3:29])[CH:27]=3)=[CH:18][CH:17]=2)([CH3:15])[CH:12]([CH3:14])[CH3:13])=[CH:9][CH:10]=1)[NH2:4].[C:30]([O:33][CH2:34][C:35](O)=[O:36])(=[O:32])[CH3:31].Cl.CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[C:30]([O:33][CH2:34][C:35]([O:1]/[N:2]=[C:3](/[NH2:4])\[C:5]1[CH:6]=[N:7][C:8]([C:11]([C:16]2[CH:21]=[CH:20][C:19]([C:22]3[CH:23]=[N:24][CH:25]=[C:26]([O:28][CH3:29])[CH:27]=3)=[CH:18][CH:17]=2)([CH3:15])[CH:12]([CH3:13])[CH3:14])=[CH:9][CH:10]=1)=[O:36])(=[O:32])[CH3:31]

Participants

7

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 83766Acetoxyacetic acidHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 72286600HCID 72286600, compound

Product 1

HCID 59393690HCID 59393690, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Compound 1a (350 mg, 0.896 mmol) was added to a stirred solution of acetoxyacetic acid (126 mg, 1.07 mmol), 1[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (205 mg, 1.07 mmol) and 1-hydroxybenzotriazole (157 mg, 1.16 mmol) in DCM (8.00 mL) at rt. After approximately 1 h, the reaction mixture was poured into saturated aqueous sodium bicarbonate and extracted with EtOAc. The combined organic extracts were washed with water and brine, dried (sodium sulfate) and concentrated in vacuo to afford the title compound 1b, which was used without further purification in the subsequent reaction. m/z (ES) 491 (MH)+ 1HNMR (500 MHz, CDCl3): δ 8.90 (s, 1H), 8.51 (s, 1H), 8.29 (s, 1H), 7.92 (d, 1H, J=8.5 Hz), 7.83 (s, 1H), 7.54 (d, 2H, J=8.0 Hz), 7.50 (d, 2H, J=8.0 Hz), 7.35 (d, 1H, J=8.3 Hz), 5.21 (br, 2H), 4.90 (s, 2H), 4.03 (s, 3H), 3.17 (m, 1H), 2.22 (s, 3H), 1.76 (s, 3H), 0.88 (d, 3H, J=6.4 Hz), 0.84 (d, 3H, J=6.6 Hz).

Workup

  1. extractionextracted with EtOAc
  2. washThe combined organic extracts were washed with water and brine
  3. dry with materialdried (sodium sulfate)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6d070695079e407ea8854eff3a7f34ba
Source dataset
uspto-grants-2013_05
Patent number
US08440672B2

Reaction notes

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