4-Methylmorpholine → {[1-(2-pyrrolidin-1-yl-ethyl)-1H-indazol-4-ylcarbamoyl]-methyl}-carbamic acid tert-butyl ester

HRID 1790084Notes

Reaction equation

HRID 1790084 reaction equation
[N:1]1([CH2:6][CH2:7][N:8]2[C:16]3[C:11](=[C:12]([NH2:17])[CH:13]=[CH:14][CH:15]=3)[CH:10]=[N:9]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[C:18]([O:22][C:23]([NH:25][CH2:26][C:27](O)=[O:28])=[O:24])([CH3:21])([CH3:20])[CH3:19].Cl.C(N=C=NC(C)(C)CC)C.ON1C2C=CC=CC=2N=N1.CN1CCOCC1>CN(C=O)C>[C:18]([O:22][C:23](=[O:24])[NH:25][CH2:26][C:27](=[O:28])[NH:17][C:12]1[CH:13]=[CH:14][CH:15]=[C:16]2[C:11]=1[CH:10]=[N:9][N:8]2[CH2:7][CH2:6][N:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1)([CH3:21])([CH3:19])[CH3:20]

Participants

7

Reactant 5

HCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 78288N-(tert-butoxycarbonyl)glycineHCID 114923411-(2-Pyrrolidin-1-YL-ethyl)-1H-indazol-4-ylamineHCID 22992078Ethyldimethylpropylcarbodiimide hydrochloride

Product 1

HCID 69652714{[1-(2-pyrrolidin-1-yl-ethyl)-1H-indazol-4-ylcarbamoyl]-methyl}-carbamic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1-(2-Pyrrolidin-1-yl-ethyl)-1H-indazol-4-ylamine (1.00 g, 4.34 mmol), tert-butoxycarbonylamino-acetic acid (0.836 g, 4.77 mmol), ethyldimethylpropylcarbodiimide hydrochloride (1.00 g, 5.24 mmol), N-hydroxybenzotriazole (0.707 g, 5.24 mmol) and N-methyl morpholine (1.10 g, 10.9 mmol) were dissolved in 30 mL of DMF, and stirred at room temperature for 6 hours. The mixture was concentrated under reduced pressure and the residue purified by flash chromatography to provide the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 1.41 (s, 9H), 1.62 (m, 4H), 2.44 (m, 4H), 2.86 (t, 2H, J=6.78), 3.86 (d, 2H, J=6.11), 4.47 (t, 2H, J=6.78), 7.08–7.65 (m, 4H), 8.24 (s, 1H), 9.97 (s, 1H); MS (DCI/NH3) m/z 388 [M+H]+.

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. customthe residue purified by flash chromatography

Sources & evidence

ORD record
ord-0705d34c04cb4ed8b8b6199abebc8b59
Source dataset
uspto-grants-2006_07
Patent number
US07071182B2

Reaction notes

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