1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 67235189, compound

HRID 1748359Notes

Reaction equation

[CH3:1][C:2]1([CH3:19])[N:7]2[C:8]3[CH:9]=[C:10]([C:15]([OH:17])=O)[CH:11]=[CH:12][C:13]=3[CH:14]=[C:6]2[C:5](=[O:18])[NH:4][CH2:3]1.ON1C2C=CC=CC=2N=N1.C(N=C=NCCCN(C)C)C.[CH2:41]([O:43][C:44]([C:46]1[N:47]([CH3:52])[CH:48]=[C:49]([NH2:51])[N:50]=1)=[O:45])[CH3:42].C(N(CC)C(C)C)(C)C>CN(C=O)C.CN(C)C1C=CN=CC=1>[CH3:1][C:2]1([CH3:19])[N:7]2[C:8]3[CH:9]=[C:10]([C:15]([NH:51][C:49]4[N:50]=[C:46]([C:44]([O:43][CH2:41][CH3:42])=[O:45])[N:47]([CH3:52])[CH:48]=4)=[O:17])[CH:11]=[CH:12][C:13]=3[CH:14]=[C:6]2[C:5](=[O:18])[NH:4][CH2:3]1

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 4,4-dimethyl-1-oxo-1,2,3,4-tetrahydropyrazino[1,2-a]indole-7-carboxylic acid (336 mg, 1.3 mmol, Intermediate E) in DMF (1 mL) are added N-hydroxybenzotriazole (351 mg, 2.6 mmol) and 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide (498 mg, 2.6 mmol). After stifling for 10 min, 4-amino-1-methyl-1H-imidazole-2-carboxylic acid ethyl ester (535 mg, 2.6 mmol), N,N-diisopropylethylamine (0.45 mL, 2.6 mmol) and 4-dimethylaminopyridine (32 mg, 0.26 mmol) are added. The reaction mixture is heated at 60° C. for 16 h. DMF is removed under a stream of N2 at 40° C. and EtOAc (2 mL) and water (2 mL) are added. After stirring for 15 min, a white solid is formed and it is filtered and dried to afford the title compound (490 mg, 92%).

Workup

customDMF is removed under a stream of N2 at 40° C.
additionEtOAc (2 mL) and water (2 mL) are added
customa white solid is formed
filtrationit is filtered
customdried

Sources & evidence

ORD record: ord-f1bab8ce37544e6ca39bf6243a8c0b74
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09150577B2

Reaction notes

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