tert-Butyl (3-aminopropyl)carbamate → (+/-)-{3-[(3-Benzyl-5-chloro-4-oxo-3,4-dihydro-pyrrolo[2,1-f][1,2,4]triazin-2-ylmethyl)-amino]-propyl}-carbamic acid tert-butyl ester

HRID 1796002Notes

Reaction equation

HRID 1796002 reaction equation
[CH2:1]([N:8]1[C:13](=[O:14])[C:12]2=[C:15]([Cl:18])[CH:16]=[CH:17][N:11]2[N:10]=[C:9]1[CH:19]=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:21]([O:25][C:26](=[O:32])[NH:27][CH2:28][CH2:29][CH2:30][NH2:31])([CH3:24])([CH3:23])[CH3:22].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>CCO>[C:21]([O:25][C:26](=[O:32])[NH:27][CH2:28][CH2:29][CH2:30][NH:31][CH2:19][C:9]1[N:8]([CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[C:13](=[O:14])[C:12]2=[C:15]([Cl:18])[CH:16]=[CH:17][N:11]2[N:10]=1)([CH3:24])([CH3:22])[CH3:23]

Participants

5

Reactant 3

HCID 2735700tert-Butyl (3-aminopropyl)carbamateHCID 5049666Sodium triacetoxyborohydrideHCID 221800693-Benzyl-5-chloro-4-oxo-3,4-dihydro-pyrrolo[2,1-f][1,2,4]triazine-2-carbaldehyde

Product 1

HCID 69591865(+/-)-{3-[(3-Benzyl-5-chloro-4-oxo-3,4-dihydro-pyrrolo[2,1-f][1,2,4]triazin-2-ylmethyl)-amino]-propyl}-carbamic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 3-benzyl-5-chloro-4-oxo-3,4-dihydro-pyrrolo[2,1-f][1,2,4]triazine-2-carbaldehyde (Example 22 E, 50 mg, 0.17 mmol) in EtOH (1 mL) was added 4 A molecular sieves (50 mg), (3-amino-propyl)-carbamic acid tert-butyl ester (Fluka, 33 mg, 0.19 mmol) and NaBH(OAc)3 (55 mg, 0.26 mmol) under Ar. The reaction mixture was stirred at rt for 2 h, filtered and the filtrate was concentrated in vacuo. The residue was purified by flash column chromatography (SiO2, 1–2% MeOH/CHCl3) to afford the desired compound, as a colorless oil (12 mg, 16%): MS (ESI+) 446 (M++H).

Workup

  1. filtrationfiltered
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe residue was purified by flash column chromatography (SiO2, 1–2% MeOH/CHCl3)

Sources & evidence

ORD record
ord-602786185edc486d808bed578df57bd5
Source dataset
uspto-grants-2006_04
Patent number
US07030118B2

Reaction notes

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