1,2-Dichloroethane → [2-Methyl-2-({4-[2-(6-methyl-pyridin-2-yl)-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl]-quinoline-7-carbonyl}-amino)-propyl]-carbamic Acid Tert-Butyl Ester

HRID 8241Notes

Reaction equation

HRID 8241 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([C:8]2[C:9]([C:16]3[C:25]4[C:20](=[CH:21][C:22]([C:26](O)=[O:27])=[CH:23][CH:24]=4)[N:19]=[CH:18][CH:17]=3)=[C:10]3[CH2:15][CH2:14][CH2:13][N:11]3[N:12]=2)[CH:5]=[CH:4][CH:3]=1.[C:29]([O:33][C:34](=[O:41])[NH:35][CH2:36][C:37]([NH2:40])([CH3:39])[CH3:38])([CH3:32])([CH3:31])[CH3:30].C(Cl)CCl.ON1C2C=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C>ClCCl>[C:29]([O:33][C:34](=[O:41])[NH:35][CH2:36][C:37]([CH3:39])([NH:40][C:26]([C:22]1[CH:21]=[C:20]2[C:25]([C:16]([C:9]3[C:8]([C:6]4[CH:5]=[CH:4][CH:3]=[C:2]([CH3:1])[N:7]=4)=[N:12][N:11]4[CH2:13][CH2:14][CH2:15][C:10]=34)=[CH:17][CH:18]=[N:19]2)=[CH:24][CH:23]=1)=[O:27])[CH3:38])([CH3:32])([CH3:30])[CH3:31]

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 101337374-[2-(6-methyl-pyridin-2-yl)-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl]-quinoline-7-carboxylic acidHCID 17909918tert-butyl N-(2-amino-2-methylpropyl)carbamate

Product 1

HCID 69365708[2-Methyl-2-({4-[2-(6-methyl-pyridin-2-yl)-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl]-quinoline-7-carbonyl}-amino)-propyl]-carbamic Acid Tert-Butyl EsterYield 91%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-[2-(6-methyl-pyridin-2-yl)-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl]-quinoline-7-carboxylic acid (0.16 g, 0.43 mmol), (2-amino-2-methyl-propyl)-carbamic acid tert-butyl ester (0.09 g, 0.47 mmol), EDC (0.09 g, 0.47 mmol), 1-hydroxybenzotriazole (0.06 g, 0.47 mmol) in dichloromethane (8.6 mL) is added N,N-diisopropylethylamine (0.25 mL, 1.29 mmol). The mixture is stirred at room temperature for 18 hand concentrated in vacuo. The residue is taken up in ethyl acetate, washed with water and saturated aqueous sodium chloride, dried over sodium sulfate and concentrated in vacuo. The residue is chromatographed on SiO2 (methanol/dichloromethane/2:98) to yield the title compound 0.21 g (91%) as a white solid.

Workup

  1. concentrationconcentrated in vacuo
  2. washwashed with water and saturated aqueous sodium chloride
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue is chromatographed on SiO2 (methanol/dichloromethane/2:98)

Sources & evidence

ORD record
ord-30f0c1b87db9430091f5e9eccc27e8b7
Source dataset
uspto-grants-2006_08
Patent number
US07087626B2

Reaction notes

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