1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 86731460, compound

HRID 509080Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:23]=[C:22]3[C:17]([CH:18]=[C:19]([C:24](O)=[O:25])[N:20]=[CH:21]3)=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH:27]1[CH:32]=[N:31][C:30]2N(O)N=[N:35][C:29]=2[CH:28]=1.[CH3:37]CN=C=NCCCN(C)C.CCN(C(C)C)C(C)C>CN(C=O)C>[NH2:35][C:29]1[CH:28]=[CH:27][CH:32]=[CH:37][C:30]=1[NH:31][C:24]([C:19]1[N:20]=[CH:21][C:22]2[C:17]([CH:18]=1)=[CH:16][CH:15]=[C:14]([N:11]1[CH2:10][CH2:9][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH2:13][CH2:12]1)[CH:23]=2)=[O:25]

Participants

Conditions

Temperature: 55 °C

Procedure

A mixture of 7-(4-(tert-butoxycarbonyl)piperazin-1-yl)isoquinoline-3-carboxylic acid (214 mg, 0.6 mmol), amine (65 mg, 0.6 mmol), HOAT (122 mg, 0.9 mmol), EDCI (229 mg, 1.2 mmol), and DIPEA (155 mg, 1.2 mmol) in DMF(5 mL) was stirred at 55° C. overnight. The mixture was quenched with water (20 mL) and extracted with EA(25 mL×2). The combined organic layers were separated, dried, filtered, and concentrated to a residue, which was purified by Pre-TLC to afford compound tert-butyl 4-(3-(2-aminophenylcarbamoyl)-isoquinolin-7-yl)piperazine-1-carboxylate (201 mg, 75%) as a yellow solid.

Workup

customThe mixture was quenched with water (20 mL)
extractionextracted with EA(25 mL×2)
customThe combined organic layers were separated
customdried
filtrationfiltered
concentrationconcentrated to a residue, which
customwas purified by Pre-TLC

Sources & evidence

ORD record: ord-356cd279eb69438188d3286fee13f138
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09096549B2

Reaction notes

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