Triethylamine → HCID 69591791, compound

HRID 1795968Notes

Reaction equation

HRID 1795968 reaction equation
[C:1]([O:5][C:6](=[O:12])[NH:7][CH2:8][CH2:9][CH2:10][NH2:11])([CH3:4])([CH3:3])[CH3:2].[CH3:13][O:14][C:15]([C:17]1[CH:18]=[CH:19][N:20]2[C:25]=1[C:24](=[O:26])[N:23]([CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:22]([CH:34](OS(C)(=O)=O)[CH2:35][CH3:36])=[N:21]2)=[O:16].C(N(CC)CC)C>CN(C=O)C>[CH3:13][O:14][C:15]([C:17]1[CH:18]=[CH:19][N:20]2[C:25]=1[C:24](=[O:26])[N:23]([CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:22]([CH:34]([NH:11][CH2:10][CH2:9][CH2:8][NH:7][C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:12])[CH2:35][CH3:36])=[N:21]2)=[O:16]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 2735700tert-Butyl (3-aminopropyl)carbamateHCID 87902786HCID 87902786, compound

Product 1

HCID 69591791HCID 69591791, compoundYield 14%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
75 °C

Procedure

(3-Amino-propyl)-carbamic acid tert-butyl ester (Fluka, 0.054 ml, 0.31 mmol) was added to a solution of 3-benzyl-2-(1-methanesulfonyloxy-propyl)-4-oxo-3,4-dihydro-pyrrolo[2,1-f][1,2,4]triazine-5-carboxyic acid methyl ester (0.086 g, 0.21 mmol) and triethylamine (0.086 mL, 0.616 mmol) in DMF (1.0 mL) and the reaction mixture was heated to 75° C. for 4 h. The reaction mixture was quenched with saturated NaHCO3 (2 mL) and extracted with EtOAc (3×10 mL). The combined organic extracts were washed with 10% LiCl (4×10 mL), dried (Na2SO4), filtered and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel eluting with 8/1 to 1/1 hexane/EtOAc to afford the title compound (0.013 g, 14%) as a solid: 1H NMR (CDCl3) δ 6.98–7.26 (m, 8H), 5.75 (m, 1H), 4.95 (m, 2H), 3.86 (s, 3H), 3.65 (m, 1H), 3.00 (m, 2H), 2.45 (m, 1H), 2.00 (m, 1H), 1.50–1.75 (m, 4H) 1.36 (s, 9H), 0.88 (m, 3H); MS (ESI+) 498 (M++H); HRMS (ESI+) calculated: 498.2716 (M++H), found: 498.2720 (M++H).

Workup

  1. customThe reaction mixture was quenched with saturated NaHCO3 (2 mL)
  2. extractionextracted with EtOAc (3×10 mL)
  3. washThe combined organic extracts were washed with 10% LiCl (4×10 mL)
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash column chromatography on silica gel eluting with 8/1 to 1/1 hexane/EtOAc

Sources & evidence

ORD record
ord-0186febb1deb4400876bb6940901ae67
Source dataset
uspto-grants-2006_04
Patent number
US07030118B2

Reaction notes

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