1,4-Dioxane hydrochloride → (+/-)-n-(3-Amino-propyl)-n-[(3-benzyl-5-chloro-4-oxo-3,4-dihydro-pyrrolo[2,1-f][1,2,4]triazin-2-yl)-cyclopropyl-methyl]-4-chloro-benzamide, hydrochloride salt

HRID 1795982Notes

Reaction equation

HRID 1795982 reaction equation
C(OC(=O)[NH:7][CH2:8][CH2:9][CH2:10][N:11]([CH:21]([C:25]1[N:30]([CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[C:29](=[O:38])[C:28]2=[C:39]([Cl:42])[CH:40]=[CH:41][N:27]2[N:26]=1)[CH:22]1[CH2:24][CH2:23]1)[C:12](=[O:20])[C:13]1[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=1)(C)(C)C.Cl.O1CCOCC1>>[ClH:19].[NH2:7][CH2:8][CH2:9][CH2:10][N:11]([CH:21]([C:25]1[N:30]([CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[C:29](=[O:38])[C:28]2=[C:39]([Cl:42])[CH:40]=[CH:41][N:27]2[N:26]=1)[CH:22]1[CH2:23][CH2:24]1)[C:12](=[O:20])[C:13]1[CH:14]=[CH:15][C:16]([Cl:19])=[CH:17][CH:18]=1

Participants

3

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 69591786{3-[[(3-Benzyl-5-chloro-4-oxo-3,4-dihydro-pyrrolo[2,1-f][1,2,4]triazin-2-yl) cyclopropyl-methyl]-(4-chloro-benzoyl)-amino]-propyl}-carbamic acid tert-butyl ester

Product 1

HCID 131725699(+/-)-n-(3-Amino-propyl)-n-[(3-benzyl-5-chloro-4-oxo-3,4-dihydro-pyrrolo[2,1-f][1,2,4]triazin-2-yl)-cyclopropyl-methyl]-4-chloro-benzamide, hydrochloride saltYield 167%

Procedure

{3-[[(3-Benzyl-5-chloro-4-oxo-3,4-dihydro-pyrrolo[2,1-f][1,2,4]triazin-2-yl) cyclopropyl-methyl]-(4-chloro-benzoyl)-amino]-propyl}-carbamic acid tert-butyl ester (8 mg) was treated with 4 N HCl/dioxane (1 mL) and the resulting mixture stirred at room temperature for 18 h. The mixture was concentrated under high vacuum to give the title compound (6 mg) as a white solid: 1H NMR (DMSO-d6) δ −0.35 (m, 1H), 0.40 (m, 1H), 0.50 (m, 1H), 0.57 (m, 1H), 1.53 (m, 1H), 1.80 (m, 1H), 1.89 (m, 1H), 2.56 (m, 2H), 3.56 (m, 2H), 4.85 (m, 1H), 5.16 (m, 1H), 5.80 (m, 1H), 6.66 (m, 1H), 7.23 (bs, 3H), 7.25 (m, 2H), 7.30–7.40 (m, 4H), 7.46–7.49 (m, 3H), 7.56 (m, 1H), 7.99 (m, 1H); HRMS (ESI+) 524.1629 (M+H)+ for C27H28N5O2Cl2.

Workup

  1. concentrationThe mixture was concentrated under high vacuum

Sources & evidence

ORD record
ord-879adb1aebf246228afa4065dbe2c28a
Source dataset
uspto-grants-2006_04
Patent number
US07030118B2

Reaction notes

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