Dimethylformamide → HCID 69652664, compound

HRID 1790094Notes

Reaction equation

HRID 1790094 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]([OH:12])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.C(N=[C:17]=[N:18][C:19]([CH3:23])(C)[CH2:20][CH3:21])C.ON1C2C=CC=[CH:33][C:28]=2[N:27]=N1.[CH3:34][N:35]1[CH2:40][CH2:39][O:38][CH2:37][CH2:36]1.[CH3:41][N:42](C=O)C>>[C:1]([O:5][C:6](=[O:7])[NH:8][CH2:9][C:10](=[O:12])[NH:27][C:28]1[CH:33]=[CH:21][CH:20]=[C:19]2[C:23]=1[CH:41]=[N:42][N:18]2[CH2:17][CH2:34][N:35]1[CH2:40][CH2:39][O:38][CH2:37][CH2:36]1)([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 5

HCID 6228DimethylformamideHCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 78288N-(tert-butoxycarbonyl)glycineHCID 22992078Ethyldimethylpropylcarbodiimide hydrochloride

Product 1

HCID 69652664HCID 69652664, compound

Procedure

A mixture of 1-(2-morpholin-1-yl-ethyl)-1H-indazol-4-ylamine (0.150 g, 0.609 mmol), tert-butoxycarbonylamino-acetic acid (0.109 g, 0.548 mmol), ethyldimethylpropylcarbodiimide hydrochloride (0.126 g, 0.660 mmol), N-hydroxybenzotriazole (0.0884 g, 0.657 mmol) and N-methyl morpholine (0.150 mL, 1.33 mmol) in 3.6 mL of DMF was 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, 9 H), 2.41 (m, 4 H), 2.75 (t, J=6.61 Hz, 2 H), 3.49 (m, 4 H), 3.86 (d, J=6.10 Hz, 2 H), 4.49 (t, J=6.61 Hz, 2 H), 7.08 (s, 1 H), 7.33 (m, 2 H), 7.64 (m, 1 H), 8.24 (s, 1 H), 9.97 (s, 1 H); MS (DCI/NH3) m/z 404 [M+H]+.

Workup

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

Sources & evidence

ORD record
ord-8fffc72fd57b49f284ad0ff03fffb3d0
Source dataset
uspto-grants-2006_07
Patent number
US07071182B2

Reaction notes

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