1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → HCID 68175188, compound

HRID 2404208Notes

Reaction equation

Cl.[C:2]([CH:6]1[CH2:11][CH2:10][CH:9]([O:12][C:13]2[CH:14]=[C:15]3[C:20](=[CH:21][CH:22]=2)[CH2:19][NH:18][CH2:17][CH2:16]3)[CH2:8][CH2:7]1)([CH3:5])([CH3:4])[CH3:3].[C:23]([O:27][C:28](=[O:42])[CH2:29][CH:30]([NH:34][C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])[C:31](O)=[O:32])([CH3:26])([CH3:25])[CH3:24].Cl.CN(C)CCCN=C=NCC.C1C=C2N=NN(O)C2=CC=1.O>CN(C=O)C.CCOCC.C(N(CC)CC)C>[C:23]([O:27][C:28](=[O:42])[CH2:29][CH:30]([NH:34][C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])[C:31]([N:18]1[CH2:17][CH2:16][C:15]2[C:20](=[CH:21][CH:22]=[C:13]([O:12][CH:9]3[CH2:10][CH2:11][CH:6]([C:2]([CH3:5])([CH3:3])[CH3:4])[CH2:7][CH2:8]3)[CH:14]=2)[CH2:19]1)=[O:32])([CH3:26])([CH3:25])[CH3:24]

Participants

Conditions

Temperature: 50 °C

Procedure

A mixture of 6-(4-tert-butyl-cyclohexyloxy)-1,2,3,4-tetrahydro-isoquinoline HCl salt, (80 mg, 0.25 mmol), 2-tert-butoxycarbonylamino-succinic acid 4-tert-butyl ester (143 mg, 0.49 mmol), triethylamine (41 uL), N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (57 mg, 0.30 mmol) and HOBT monohydrate (10 mg, 0.06 mmol) in DMF (2.0 mL) was heated at 50° C. for 4 hrs. The solution was diluted with ether and washed with water. The organic phase was dried over MgSO4, filtered and concentrated. The residue was purified via a silica gel column eluted with EtOAc in hexanes from 0 to 20% to give desired product (90 mg, yield: 65%).

Workup

washwashed with water
dry with materialThe organic phase was dried over MgSO4
filtrationfiltered
concentrationconcentrated
customThe residue was purified via a silica gel column
washeluted with EtOAc in hexanes from 0 to 20%

Sources & evidence

ORD record: ord-84d78f1a16c242e895ef2c8847cbc2bf
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08802659B2

Reaction notes

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