Triethylamine → HCID 66889465, compound

HRID 1895547Notes

Reaction equation

[CH2:1]([O:8][C:9]([N:11]1[CH2:20][CH2:19][C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]1[C:21](O)=[O:22])=[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.[NH2:53][C:54]1[C:62]([NH2:63])=[CH:61][CH:60]=[CH:59][C:55]=1[C:56]([NH2:58])=[O:57]>CN(C=O)C>[NH2:53][C:54]1[C:55]([C:56](=[O:57])[NH2:58])=[CH:59][CH:60]=[CH:61][C:62]=1[NH:63][C:21]([CH:12]1[C:13]2[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:19][CH2:20][N:11]1[C:9]([O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:10])=[O:22]

Participants

Conditions

Temperature: 55 °C

Procedure

Step-1: To a solution of 2-((benzyloxy)carbonyl)-1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid (560 mg, 1.8 mmol) in anhydrous DMF (7 ml) was added EDC.HCl (1.035 g, 5.4 mmol), HOAt (367 mg, 2.7 mmol) and triethylamine (0.375 ml, 2.7 mmol) at RT and the mixture was stirred for 10 min. To this reaction mixture, 2,3-diaminobenzamide (302 mg, 2 mmol) was added and heated to 55° C. over night. The reaction mixture was poured into ice cold water and stirred for 30 min. The precipitate formed was filtered and dried under vacuum to yield benzyl 1-((2-amino-3-carbamoylphenyl)carbamoyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate. MS (ES+): m/z 445.22 [M+H]+

Workup

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

Sources & evidence

ORD record: ord-213d987e4ad84355aaf167a56a2d7a07
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08513433B2

Reaction notes

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