Hydrochloric Acid → AF-DX-384

HRID 2351451Notes

Reaction equation

HRID 2351451 reaction equation
Cl[C:2]([N:4]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[C:8](=[O:15])[NH:7][C:6]2[CH:16]=[CH:17][CH:18]=[N:19][C:5]1=2)=[O:3].[CH2:20]([N:23]([CH2:27][CH:28]1[CH2:33][CH2:32][CH2:31][CH2:30][N:29]1[CH2:34][CH2:35][NH2:36])[CH2:24][CH2:25][CH3:26])[CH2:21][CH3:22].Cl>C(#N)C>[CH2:20]([N:23]([CH2:27][CH:28]1[CH2:33][CH2:32][CH2:31][CH2:30][N:29]1[CH2:34][CH2:35][NH:36][C:2]([N:4]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[C:8](=[O:15])[NH:7][C:6]2[CH:16]=[CH:17][CH:18]=[N:19][C:5]1=2)=[O:3])[CH2:24][CH2:25][CH3:26])[CH2:21][CH3:22]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 108684382-[2-[(Dipropylamino)methyl]-piperidin-1-yl]ethanamineHCID 1104396211-chlorocarbonyl-5,11-dihydro-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one

Product 1

HCID 119357AF-DX-384Yield 60%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Prepared analogously to Example 2 from 11-(chlorocarbonyl)-5,11-dihydro-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one and (+)-2-[2-[(dipropylamino)methyl]-piperidin-l-yl]ethanamine in a yield of 60% of theory. Colourless crystals, m.p. 164°-165° C. (acetonitrile); [α]D20 =+7.24° (dilute aqueous hydrochloric acid).

Sources & evidence

ORD record
ord-911fa773a1f743cf9bab84c0e5186095
Source dataset
uspto-grants-1989_10
Patent number
US04873236

Reaction notes

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