1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → HCID 178451119, compound

HRID 2404110Notes

Reaction equation

[C:1]([CH:5]1[CH2:10][CH2:9][CH:8]([O:11][C:12]2[CH:13]=[C:14]3[C:18](=[CH:19][CH:20]=2)[NH:17][CH2:16][CH2:15]3)[CH2:7][CH2:6]1)([CH3:4])([CH3:3])[CH3:2].C1C=C2N=NN(O)C2=CC=1.O.[C:32]([O:36][C:37](=[O:51])[CH2:38][CH:39]([NH:43][C:44]([O:46][C:47]([CH3:50])([CH3:49])[CH3:48])=[O:45])[C:40](O)=[O:41])([CH3:35])([CH3:34])[CH3:33].Cl.CN(C)CCCN=C=NCC>CN(C)C=O.CCOCC>[C:32]([O:36][C:37](=[O:51])[CH2:38][CH:39]([NH:43][C:44]([O:46][C:47]([CH3:50])([CH3:49])[CH3:48])=[O:45])[C:40]([N:17]1[C:18]2[C:14](=[CH:13][C:12]([O:11][C@H:8]3[CH2:9][CH2:10][C@H:5]([C:1]([CH3:4])([CH3:2])[CH3:3])[CH2:6][CH2:7]3)=[CH:20][CH:19]=2)[CH2:15][CH2:16]1)=[O:41])([CH3:35])([CH3:34])[CH3:33]

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of 5-(4-tert-butyl-cyclohexyloxy)-2,3-dihydro-1H-indole (110 mg, 0.4 mmol) in dimethylformamide (2 mL) was added HOBT monohydrate (10 mg, 0.1 mmol), 2-tert-butoxycarbonylamino-succinic acid 4-tert-butyl ester (230 mg, 0.8 mmol) and finally N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (92 mg, 0.48 mmol). The reaction was heated at 50° C. overnight. The solution was diluted with ether and washed twice with water. The organic phase was dried over MgSO4, filtered and concentrated to give crude product (220 mg, yield: 100%). The crude was used directly in Example 53. ESI-MS: 545.4 (M+H)+.

Workup

washwashed twice with water
dry with materialThe organic phase was dried over MgSO4
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-cb9639534ea04727a5882d58a3e83016
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08802659B2

Reaction notes

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