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

HRID 906191Notes

Reaction equation

HRID 906191 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]([CH2:43][CH3:44])[CH:28]=1)#[N:26].C([Mg]Cl)C>>[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]([CH2:43][CH3:44])[CH:28]=1)=[O:10]

Participants

5

Reactant 4

HCID 2724537(R)-sec-butylamineHCID 67403700ethyl 4-cyano-2-ethyl-5-{[(1R)-1-methylpropyl]amino}benzoateHCID 67404527ethyl 2-bromo-4-cyano-5-{[(1R)-1-methylpropyl]amino}benzoateHCID 178461633HCID 178461633, compound

Product 1

HCID 577481804-(aminocarbonyl)-2-ethyl-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-ethyl-5-{[(1R)-1-methylpropyl]amino}benzoate by treatment with ethylmagnesium chloride according to the method described in Synlett 1996, 5, 473-474 then proceeding through steps 3 and 4. 1H NMR (400 MHz, DMSO-d6): 7.94 (s, 1H), 7.81 (d, 1H), 7.49 (s, 1H), 7.27 (s, 1H), 6.98 (s, 1H), 2.67-2.75 (m, 2H), 1.44-1.53 (m, 2H), 1.06-1.15 (m, 6H), 0.89 (t, 3H).

Workup

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

Sources & evidence

ORD record
ord-086be0693e56451a8f73524dd73d6647
Source dataset
uspto-grants-2011_09
Patent number
US08012956B2

Reaction notes

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