Triethylamine → HCID 66888570, compound

HRID 1895555Notes

Reaction equation

[CH2:1]([O:8][C:9]([N:11]1[C:20]([CH3:24])([C:21](O)=[O:22])[CH2:19][C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCN=C=NCCCN(C)C.Cl.C1C=NC2N(O)N=NC=2C=1.C(N(CC)CC)C.[NH2:54][C:55]1[C:63]([NH2:64])=[CH:62][CH:61]=[CH:60][C:56]=1[C:57]([NH2:59])=[O:58]>CN(C=O)C>[NH2:54][C:55]1[C:56]([C:57](=[O:58])[NH2:59])=[CH:60][CH:61]=[CH:62][C:63]=1[NH:64][C:21]([C:20]1([CH3:24])[CH2:19][C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH2:12][N:11]1[C:9]([O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)=[O:10])=[O:22]

Participants

Conditions

Temperature: 55 °C

Procedure

Step-4: To a solution of 2-((benzyloxy)carbonyl)-3-methyl-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid (620 mg, 1.91 mmol) in anhydrous DMF (5 ml) was added EDC.HCl (1.098 mg, 5.73 mmol), HOAt (390 mg, 2.87 mmol) and triethylamine (0.4 ml, 2.87 mmol) at RT and the mixture was stirred for 10 min. To this reaction mixture, 2,3-diaminobenzamide (346 mg, 2.29 mmol) was added and heated to 55° C. for 3 days. The reaction mixture was poured into ice cold water and stirred for 30 min. The precipitate formed was filtered and dried under vacuum and purified by preparative TLC using ethyl acetate as eluent to afford benzyl 3-((2-amino-3-carbamoylphenyl)carbamoyl)-3-methyl-3,4-dihydroisoquinoline-2(1H)-carboxylate. MS (ES+): m/z 481.2 [M+Na]+

Workup

additionThe reaction mixture was poured into ice cold water
stirringstirred for 30 min
customThe precipitate formed
filtrationwas filtered
customdried under vacuum
custompurified by preparative TLC

Sources & evidence

ORD record: ord-bf6d4fc751aa44928a6d9fe568ad3d8e
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08513433B2

Reaction notes

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