O-Phenylenediamine → HCID 86731465, compound

HRID 509087Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[C:23]([CH:24]3[CH2:26][CH2:25]3)=[C:22]3[C:17]([CH:18]=[C:19]([C:27]([OH:29])=O)[N:20]=[CH:21]3)=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:30]1([NH2:37])[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=1[NH2:36].C1C=NC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.CCN(C(C)C)C(C)C>CN(C=O)C>[NH2:36][C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][C:30]=1[NH:37][C:27]([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]([CH3:3])([CH3:2])[CH3:4])=[O:7])[CH2:13][CH2:12]1)[C:23]=2[CH:24]1[CH2:25][CH2:26]1)=[O:29]

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 7-(4-(tert-butoxycarbonyl)piperazin-1-yl)-8-cyclopropylisoquinoline-3-carboxylic acid (60 mg, 0.15 mmol) and o-Phenylenediamine (16 mg, 0.15 mmol) in DMF (5 mL) was added HOAT (41 mg, 0.3 mmol), EDCI (46 mg, 0.3 mmol), and DIPEA (77 mg, 0.6 mmol). The reaction mixture was stirred at 60° C. overnight. After extraction by EA, the combined organic layers were dried by anhydrous Na2SO4 and concentrated in vacuo to afford tert-butyl 4-(3-(2-aminophenylcarbamoyl)-8-cyclopropylisoquinolin-7-yl)piperazine-1-carboxylate as a yellow solid (80 mg, yield: 99%).

Workup

extractionAfter extraction by EA
dry with materialthe combined organic layers were dried by anhydrous Na2SO4
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-a03f442d587d4666a345a6742b3bc719
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09096549B2

Reaction notes

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