(R)-sec-butylamine → 4-(aminocarbonyl)-2-(ethylamino)-5-{[(1R)-1-methylpropyl]amino}benzoic acid

HRID 906190

Reaction equation

HRID 906190 reaction equation
C[C@@H](N)CC.BrC1C=C(C#N)C(N[C@H](C)CC)=CC=1C(OCC)=[O:10].[C:25]([C:27]1[C:37]([NH:38][C@H:39]([CH3:42])[CH2:40][CH3:41])=[CH:36][C:30]([C:31]([O:33]CC)=[O:32])=[C:29]([NH:43][CH2:44][CH3:45])[CH:28]=1)#[N:26]>>[NH2:26][C:25]([C:27]1[C:37]([NH:38][C@H:39]([CH3:42])[CH2:40][CH3:41])=[CH:36][C:30]([C:31]([OH:33])=[O:32])=[C:29]([NH:43][CH2:44][CH3:45])[CH:28]=1)=[O:10]

Participants

4

Reactant 3

HCID 2724537(R)-sec-butylamineHCID 67404527ethyl 2-bromo-4-cyano-5-{[(1R)-1-methylpropyl]amino}benzoateHCID 67405722ethyl 4-cyano-2-(ethylamino)-5-{[(1R)-1-methylpropyl]amino}benzoate

Product 1

HCID 577485904-(aminocarbonyl)-2-(ethylamino)-5-{[(1R)-1-methylpropyl]amino}benzoic acid

Procedure

Synthesized according to the method of reagent preparation 50 by using (1R)-1-methylpropylamine in step 1 then following step 2 with the conversion of ethyl 2-bromo-4-cyano-5-{[(1R)-1-methylpropyl]amino}benzoate to ethyl 4-cyano-2-(ethylamino)-5-{[(1R)-1-methylpropyl]amino}benzoate according to the method described in step 1 then proceeding through steps 3 and 4. MS (EI) for C14H21N3O3: 280 (MH+).

Workup

  1. customSynthesized
  2. customaccording to the method of reagent preparation 50

Sources & evidence

ORD record
ord-445f68c7ef214569aad75372bc727aca
Source dataset
uspto-grants-2011_09
Patent number
US08012956B2

Linked notes

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