Triethylamine → HCID 69591843, compound

HRID 1796001Notes

Reaction equation

[C:1]([O:5][C:6](=[O:33])[NH:7][C:8]([CH3:32])([CH3:31])[CH2:9][NH:10][CH:11]([C:14]1[N:19]([CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:18](=[O:27])[C:17]2=[CH:28][CH:29]=[CH:30][N:16]2[N:15]=1)[CH2:12][CH3:13])([CH3:4])([CH3:3])[CH3:2].[Cl:34][C:35]1[CH:43]=[CH:42][C:38]([C:39](Cl)=[O:40])=[CH:37][CH:36]=1.CCN(CC)CC>C(Cl)(Cl)Cl>[C:1]([O:5][C:6](=[O:33])[NH:7][C:8]([CH3:32])([CH3:31])[CH2:9][N:10]([CH:11]([C:14]1[N:19]([CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:18](=[O:27])[C:17]2=[CH:28][CH:29]=[CH:30][N:16]2[N:15]=1)[CH2:12][CH3:13])[C:39](=[O:40])[C:38]1[CH:42]=[CH:43][C:35]([Cl:34])=[CH:36][CH:37]=1)([CH3:2])([CH3:3])[CH3:4]

Participants

Conditions

Temperature: 25 °C

Procedure

{2-[1-(3-Benzyl-4-oxo-3,4-dihydro-pyrrolo[2,1-f][1,2,4]triazin-2-yl)-propylamino]-1,1-dimethyl-ethyl}-carbamic acid tert-butyl ester (70 mg, 0.15 mmol) and 4-chlorobenzoylchloride (81.0 mg, 0.463 mmol) in CHCl3 (20 mL) was treated with Et3N (20.8 mg, 0.385 mmol). The reaction mixture was stirred at 25° C. for 18 h then concentrated under vacuum. The residue was and purified by preparative HPLC using a YMC S10 ODS 30×100 mm column to afford the desired material (52.2 mg, 57%) as a white powder: 1H NMR (CD3OD, 400 MHz) δ 7.55 (s, 1H), 7.45 (m, 5H), 7.08 (m, 1H), 6.67 (m, 1H), 5.87 (m, 1H), 3.93 (m, 1H), 3.72 (m, 1H), 3.48 (m, 1H), 3.30 (s, 1H), 1.81 (m, 1H), 1.38 (s, 9H), 1.17 (m, 3H), 0.90 (m, 3H), 0.54 (m, 3H); LC/MS (ESI+) 592 (M++H).

Workup

concentrationthen concentrated under vacuum
custompurified by preparative HPLC

Sources & evidence

ORD record: ord-2a414822adbe434fa1046733049a8d54
Source dataset: uspto-grants-2006_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07030118B2

Reaction notes

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