Triethylamine → HCID 24897853, compound

HRID 1819914Notes

Reaction equation

C(N(CC)CC)C.CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1.[N:29]1[CH:34]=[CH:33][C:32]([CH2:35][C:36]([OH:38])=O)=[CH:31][CH:30]=1.[CH:39]1[C:47]2[C:46]3[CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][C:45]=3[O:44][C:43]=2[CH:42]=[CH:41][C:40]=1[NH2:54]>>[CH:39]1[C:47]2[C:46]3[CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][C:45]=3[O:44][C:43]=2[CH:42]=[CH:41][C:40]=1[NH:54][C:36](=[O:38])[CH2:35][C:32]1[CH:31]=[CH:30][N:29]=[CH:34][CH:33]=1

Participants

Reactant 5

HCID 8471Triethylamine

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide

HCID 342284-Pyridineacetic acid

HCID 757711-Hydroxybenzotriazole

HCID 57890287HCID 57890287, compound

Product 1

HCID 24897853HCID 24897853, compoundYield 44.9%

Procedure

Following the procedure of Example 30, triethylamine (0.40 mL, 2.9 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide (0.33 g, 1.7 mmol), N-hydroxybenzotriazole (0.23 g, 1.7 mmol), 4-pyridylacetic acid(0.24 g, 1.4 mmol), and 6,7,8,9,10,11-hexahydro-benzo[b]-cycloocta[d]furan-2-ylamine (0.25 g, 1.2 mmol) provided N-(6,7,8,9,10,11-hexahydrobenzo[b]cycloocta[d]furan-2-yl)-2-pyridin-4-ylacetamide (0.18 g). MS (ESI) m/z 335 ([M+H]+); MS (ESI) m/z 333 ([M−H]−).

Sources & evidence

ORD record: ord-c8da4bb1e5b645b090a2c7ff3690fb8f
Source dataset: uspto-grants-2009_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07601856B2

Reaction notes

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