1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 69064943, compound

HRID 643164Notes

Reaction equation

HRID 643164 reaction equation
[CH2:1]([O:8][C:9]1[C:24]([CH3:25])=[CH:23][C:12]([CH2:13][C@@H:14]([CH2:19][C:20]([O-])=[O:21])[C:15]([O:17][CH3:18])=[O:16])=[CH:11][C:10]=1[O:26][CH3:27])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH:28]1[CH2:33][CH2:32][CH:31]([N:34]2[CH2:40][CH2:39][C:38]3[CH:41]=[CH:42][CH:43]=[CH:44][C:37]=3[NH:36][C:35]2=[O:45])[CH2:30][CH2:29]1.CN(C)CCCN=C=NCC>CN(C)C1C=CN=CC=1.C(#N)C.C1COCC1>[CH2:1]([O:8][C:9]1[C:24]([CH3:25])=[CH:23][C:12]([CH2:13][C@@H:14]([CH2:19][C:20](=[O:21])[N:28]2[CH2:29][CH2:30][CH:31]([N:34]3[CH2:40][CH2:39][C:38]4[CH:41]=[CH:42][CH:43]=[CH:44][C:37]=4[NH:36][C:35]3=[O:45])[CH2:32][CH2:33]2)[C:15]([O:17][CH3:18])=[O:16])=[CH:11][C:10]=1[O:26][CH3:27])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 3

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 113795873-(Piperidin-4-yl)-4,5-dihydro-1H-benzo[d][1,3]diazepin-2(3H)-oneHCID 86632854HCID 86632854, compound

Product 1

HCID 69064943HCID 69064943, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6342AcetonitrileSolventHCID 8028TetrahydrofuranSolvent

Procedure

Prepared analogously to Example 12d from 5.80 g (15.6 mmol) 1-methyl (S)-2-(4-benzyloxy-3-methoxy-5-methyl-benzyl)-succinate and 4.20 g (17.13 mmol) 3-piperidin-4-yl-1,3,4,5-tetrahydro-1,3-benzodiazepin-2-one, using 3.43 g (17.9 mmol) (3-dimethylamino-propyl)-ethyl-carbodiimide and 2.38 g (19.5 mmol) 4-dimethylamino-pyridine for the coupling and 130 mL acetonitrile and 50 mL THF as solvent.

Sources & evidence

ORD record
ord-4fad894f96154df9b74fee88b5d66d2a
Source dataset
uspto-grants-2010_04
Patent number
US07696209B2

Reaction notes

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