tert-Butyl (3-aminopropyl)carbamate → HCID 69591866, compound

HRID 1795958Notes

Reaction equation

HRID 1795958 reaction equation
[CH2:1]([N:8]1[C:13](=[O:14])[C:12]2=[CH:15][CH:16]=[C:17]([Cl:18])[N:11]2[N:10]=[C:9]1[CH:19]([CH:21]1[CH2:23][CH2:22]1)O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:24]([NH:31][CH2:32][CH2:33][CH2:34][NH2:35])([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25]>C1(C)C(C)=CC=CC=1>[C:27]([O:26][C:24](=[O:25])[NH:31][CH2:32][CH2:33][CH2:34][NH:35][CH:19]([C:9]1[N:8]([CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[C:13](=[O:14])[C:12]2=[CH:15][CH:16]=[C:17]([Cl:18])[N:11]2[N:10]=1)[CH:21]1[CH2:23][CH2:22]1)([CH3:30])([CH3:28])[CH3:29]

Participants

4

Reactant 2

HCID 2735700tert-Butyl (3-aminopropyl)carbamateHCID 22180051HCID 22180051, compound

Product 1

HCID 69591866HCID 69591866, compoundYield 69.3%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A solution of 3-benzyl-7-chloro-2-(cyclopropyl-hydroxy-methyl)-3H-pyrrolo[2,1-f][1,2,4]triazin-4-one (0.32 g, 0.92 mmol) and N-BOC-1,3-diaminopropane (Fluka, 1.0 g, 5.7 mmol) in xylene (12 mL) was heated at 110° C. under nitrogen for 4 days. The solvent was removed under reduced pressure. Purification of the residue by flash column chromatography (SiO2, EtOAc/hexane 1:3 to 3:2) gave the title compound as a light yellow oil (0.31 g, 62%): 1H NMR (CDCl3) δ 7.25 (m, 3H), 7.20 (m, 1H), 7.07 (d, 2H, J=7.15 Hz), 7.00 (d, 1H, J=4.95 Hz), 6.44 (d, 1H, J=4.95 Hz), 5.41 (m, 1H), 4.82 (m, 1H), 3.33 (m 1H), 3.03 (m, 2H), 2.40 (m, 2H), 1.52 (m, 2H), 1.35 (s, 9H), 1.30 (m, 2H), 1.19 (m, 2H), 0.52 (m, 1H), 0.35 (m, 1H), 0.13 (m, 1H); MS (ESI+) 486.17, 488.17 (M++H).

Workup

  1. customThe solvent was removed under reduced pressure
  2. customPurification of the residue by flash column chromatography (SiO2, EtOAc/hexane 1:3 to 3:2)

Sources & evidence

ORD record
ord-7f9c49109f8446389bfd56c7e073ac39
Source dataset
uspto-grants-2006_04
Patent number
US07030118B2

Reaction notes

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