Sodium triacetoxyborohydride → {3-[1-(3-Benzyl-4-oxo-3,4-dihydro-pyrrolo[2,1-f][1,2,4]triazin-2-yl)-propylamino]-propyl}-carbamic acid tert-butyl ester

HRID 1795994Notes

Reaction equation

[NH2:1][CH:2]([C:5]1[N:10]([CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:9](=[O:18])[C:8]2=[CH:19][CH:20]=[CH:21][N:7]2[N:6]=1)[CH2:3][CH3:4].[C:22]([O:26][C:27](=[O:33])[NH:28][CH2:29][CH2:30][CH:31]=O)([CH3:25])([CH3:24])[CH3:23].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>CO>[C:22]([O:26][C:27](=[O:33])[NH:28][CH2:29][CH2:30][CH2:31][NH:1][CH:2]([C:5]1[N:10]([CH2:11][C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:9](=[O:18])[C:8]2=[CH:19][CH:20]=[CH:21][N:7]2[N:6]=1)[CH2:3][CH3:4])([CH3:25])([CH3:24])[CH3:23]

Participants

Conditions

Temperature: 25 °C

Procedure

2-(1-Amino-propyl)-3-benzyl-3H-pyrrolo[2,1-f][1,2,4]triazin-4-one (Example 26, 300 mg, 0.94 mmol) and (3-oxo-propyl)-carbamic acid tert-butyl ester (J. Med. Chem. 1985, 28, 317–323, 982 mg, 5.64 mmol) were dissolved in CH3OH (20 mL) and stirred for 1 h at 25° C. The mixture was then treated with NaBH(OAc)3 (1.19 g, 5.64 mmol) and stirred for 18 h. The reaction mixture was concentrated under vacuum and purified by preparative HPLC using a YMC S10 ODS 30×250 mm column affording the desired compound (300 mg, 73%) as a colorless film: 13C NMR (CD3OD, 100 MHz) δ 160.8, 160.49, 154.89, 144.86, 136.06, 129.09, 128.04, 126.52, 121.79, 117.72, 115.16, 111.60, 109.53, 79.20, 57.97, 44.32, 27.38, 26.55, 25.5, 7.58; LC/MS (ESI+) 440 (M++H).

Workup

stirringstirred for 18 h
concentrationThe reaction mixture was concentrated under vacuum
custompurified by preparative HPLC

Sources & evidence

ORD record: ord-b2b8e60119124386a6516b28e6bbb2ce
Source dataset: uspto-grants-2006_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07030118B2

Reaction notes

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