1-Hydroxybenzotriazole → HCID 69334014, compound

HRID 350403Notes

Reaction equation

HRID 350403 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[NH:15][C:16](=[O:30])[NH:17][C:18]1[CH:23]=[CH:22][C:21]([CH2:24][C:25]([OH:27])=O)=[CH:20][C:19]=1[O:28][CH3:29])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH:31]1[CH2:35][CH2:34][CH2:33][CH:32]1[CH2:36][O:37][C:38]1[CH:47]=[CH:46][C:41]([C:42]([O:44][CH3:45])=[O:43])=[CH:40][C:39]=1[N+:48]([O-:50])=[O:49].C1C=CC2N(O)N=[N:57]C=2C=1.CCN=C=NCCCN(C)C.Cl>CN(C1C=CN=CC=1)C.C1COCC1.O>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[NH:15][C:16](=[O:30])[NH:17][C:18]1[CH:23]=[CH:22][C:21]([CH2:24][C:25]([NH:57][N:31]2[CH2:35][CH2:34][CH2:33][CH:32]2[CH2:36][O:37][C:38]2[CH:47]=[CH:46][C:41]([C:42]([O:44][CH3:45])=[O:43])=[CH:40][C:39]=2[N+:48]([O-:50])=[O:49])=[O:27])=[CH:20][C:19]=1[O:28][CH3:29])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 23511706HCID 23511706, compoundHCID 23512271HCID 23512271, compound

Product 1

HCID 69334014HCID 69334014, compoundYield 404.2%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-[N′-(2-benzyloxyphenyl)ureido]-3-methoxyphenylacetic acid (1.12 g, 2.76 mmol), methyl 4-(2-pyrrolidinylmethoxy)-3-nitrobenzoate (890 mg, 2.76 mmol), HOBt (74.0 mg, 0.55 mmol), DMAP (67.0 mg, 0.55 mmol), and Et3 N (0.58 mL, 4.13 mmol) in THF (15 mL) was added EDC.HCl (792 mg, 4.13 mmol). After being stirred at room temperature for 12 hr, the reaction mixture was diluted with water and extracted with EtOAc. The extracts were washed with brine, dried over Na2SO4, and concentrated to dryness. Chromatography of the residue with EtOAc as eluent gave methyl 4-[1-[4-[N′-(2-benzyloxyphenyl)ureido]-3-methoxyphenylacetamido ]-2-pyrrolidinylmethoxy]-3-nitrobenzoate (1.52 g, 82%) as a yellow amorphous solid. 1H-NMR (CDCl3) δ 1.91 (m, 1H), 1.95–2.17 (m, 3H), 3.47–3.53 (m, 2H), 3.56 (s, 2H), 3.60 (m, 1H), 3.68 (s, 3H), 3.90 (s, 3H), 4.11 (d, J=7.3 Hz, 1 H), 4.45 (m, 1H), 5.08 (s, 2H), 6.70 (dd, J=8.3, 1.9 Hz, 1H), 6.75 (d, J=1.9 Hz, 1H), 6.91–6.99 (m, 31H), 7.16 (s, 1H), 7.18 (d, J=8.3 Hz, 1H), 7.33–7.40 (m, 6H), 7.91 (d, J=8.3 Hz, 1H), 8.11–8.16 (m, 2H), 8.46 (s, 1H).

Workup

  1. extractionextracted with EtOAc
  2. washThe extracts were washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-2a01dcf0f3eb43a38b517c1295304972
Source dataset
uspto-grants-2007_02
Patent number
US07179819B2

Reaction notes

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