Sodium triacetoxyborohydride → HCID 69591886, compound

HRID 1795998Notes

Reaction equation

[C:1]([O:5][C:6](=[O:14])[NH:7][C:8]([CH3:13])([CH3:12])[CH2:9][CH:10]=O)([CH3:4])([CH3:3])[CH3:2].[NH2:15][CH:16]([C:19]1[N:24]([CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:23](=[O:32])[C:22]2=[CH:33][CH:34]=[CH:35][N:21]2[N:20]=1)[CH2:17][CH3:18].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>CO>[C:1]([O:5][C:6](=[O:14])[NH:7][C:8]([CH3:13])([CH3:12])[CH2:9][CH2:10][NH:15][CH:16]([C:19]1[N:24]([CH2:25][C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[C:23](=[O:32])[C:22]2=[CH:33][CH:34]=[CH:35][N:21]2[N:20]=1)[CH2:17][CH3:18])([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 25 °C

Procedure

(1,1-Dimethyl-3-oxo-propyl)-carbamic acid tert-butyl ester (19 mg, 0.564 mmol) and 2-(1-amino-propyl)-3-benzyl-3H-pyrrolo[2,1-f][1,2,4]triazin-4-one (Example 26, 120 mg, 0.376 mmol) were stirred in CH3OH (10 mL) for 1 h at 25° C. The mixture was then treated with NaBH(OAc)3 (119 mg, 0.564 mmol) and stirred for 12 h at 25° C. The mixture was concentrated under vacuum and purified by preparative HPLC using a YMC S10 ODS 30×100 mm column affording the desired material (100 mg, 57%) as a colorless oil: 13C NMR (CDCl3 100 MHz) δ 161.54, 154.93, 154.42, 144.72, 135.84, 129.53, 128.58, 127.27, 121.99, 117.28, 114.95, 111.94, 110.48, 79.81, 58.05, 51.12, 44.61, 43.07, 35.91, 28.17, 27.07, 26.53, 8.55; LC/MS (ESI+) 468 (M++H).

Workup

concentrationThe mixture was concentrated under vacuum
custompurified by preparative HPLC

Sources & evidence

ORD record: ord-389b9d22e5514efc873426f95b52e4ba
Source dataset: uspto-grants-2006_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07030118B2

Reaction notes

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