4-Methylmorpholine → HCID 22138931, compound

HRID 1825817Notes

Reaction equation

HRID 1825817 reaction equation
[N:1]1([CH2:6][CH2:7][N:8]2[CH:16]=[C:15]3[C:10]([CH:11]=[CH:12][CH:13]=[C:14]3N)=[N:9]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH2:18]([O:25][C:26]1[CH:31]=[CH:30][C:29]([CH2:32][C:33]([OH:35])=O)=[CH:28][CH:27]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.Cl.[CH2:37]([N:39]=C=NC(C)(C)CC)C.ON1C2C=CC=CC=2N=N1.CN1CCOCC1>CN(C)C=O>[CH2:18]([O:25][C:26]1[CH:31]=[CH:30][C:29]([CH2:32][C:33]([NH:39][CH2:37][C:14]2[C:15]3[C:10]([CH:11]=[CH:12][CH:13]=2)=[N:9][N:8]([CH2:7][CH2:6][N:1]2[CH2:5][CH2:4][CH2:3][CH2:2]2)[CH:16]=3)=[O:35])=[CH:28][CH:27]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

7

Reactant 5

HCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 810334-Benzyloxyphenylacetic acidHCID 11401973HCID 11401973, compoundHCID 22992078Ethyldimethylpropylcarbodiimide hydrochloride

Product 1

HCID 22138931HCID 22138931, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A 10 mL culture tube with screw cap was charged with 2-(2-pyrrolidin-1-yl-ethyl)-2H-indazol-4-ylamine (56.0 mg, 0.243 mmol), (4-benzyloxy-phenyl)-acetic acid (60.0 mg, 0.248 mmol), ethyldimethylpropylcarbodiimide hydrochloride (57.0 mg, 0.298 mmol), N-hydroxybenzotriazole (40.0 mg, 0.296 mmol), N-methyl morpholine (64.0 mg, 0.633 mmol), 2 mL of N,N-dimethylformamide and the reaction vessel placed on a shaker for 6 hours. After this time, the N,N-dimethylformamide was removed in vacuo and the residue was dissolved in 1.5 mL of a 1:1 mixture of dimethyl sulfoxide/methanol and purified by preparative reverse-phase HPLC. 1H NMR (300 MHz, DMSO-d6) δ ppm 1.70 (m, 4H), 2.60 (m, 4H), 3.10 (s, 2H), 3.68 (s, 2H), 4.48 (t, 2H, J=6.44), 5.09 (s, 2H), 6.97 (m, 2H), 7.12–7.45 (m, 9H), 7.51 (m, 1H), 8.49 (s, 1H), 10.03 (s, 1H); MS (DCI/NH3) m/z 455 [M+H]+.

Workup

  1. customA 10 mL culture tube with screw cap
  2. customAfter this time, the N,N-dimethylformamide was removed in vacuo
  3. dissolutionthe residue was dissolved in 1.5 mL of a 1:1 mixture of dimethyl sulfoxide/methanol
  4. custompurified by preparative reverse-phase HPLC

Sources & evidence

ORD record
ord-c89da0064c3146b98df9c86f281e7180
Source dataset
uspto-grants-2006_05
Patent number
US07049307B2

Reaction notes

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