Hydrochloric Acid → HCID 89544798, compound

HRID 2283422Notes

Reaction equation

HRID 2283422 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]([NH:11][C@@H:12]([CH3:17])[CH2:13][C:14]([NH2:16])=[O:15])[CH2:9][CH3:10])=[C:4]([F:18])[C:3]=1[C:19]([C:21]1[CH:26]=[CH:25]C(C#N)=[CH:23][CH:22]=1)=[O:20].Cl.CC[O:32][C:33]([CH3:35])=[O:34]>>[C:14]([CH2:13][C@@H:12]([NH:11][C@@H:8]([C:5]1[C:4]([F:18])=[C:3]([C:19]([C:21]2[CH:26]=[CH:25][C:35]([C:33]([OH:32])=[O:34])=[CH:23][CH:22]=2)=[O:20])[C:2]([Cl:1])=[CH:7][CH:6]=1)[CH2:9][CH3:10])[CH3:17])(=[O:15])[NH2:16]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 89544492HCID 89544492, compound

Product 1

HCID 89544798HCID 89544798, compound

Procedure

To (3S)-3-{[(1R)-1-{4-chloro-3-[(4-cyanophenyl)carbonyl]-2-fluorophenyl}propyl]amino}-butanamide (compound of Example 91) (0.024 g, 0.06 mmol) added EtOAc (0.1 ml) and 6M HCl (0.1 ml)stirred at ambient 48 hours, evaporated down, residue dissolved in DMSO (0.1 ml) treated with K2CO3 (spatula end) stirred ambient for 16 hours, some primary amide product visible, further DMSO (0.1 ml) and 2M NaOH (0.2 ml) added stirred ambient 16 hours to give predominantly the acid. Reaction products purified by Prep HPLC to give 4-({3-[(1R)-1-{[(2S)-1-carbamoylpropan-2-yl]amino}propyl]-6-chloro-2-fluorophenyl}carbonyl)-benzoic acid (0.09 g).

Workup

  1. customevaporated down
  2. dissolutionresidue dissolved in DMSO (0.1 ml)
  3. additiontreated with K2CO3 (spatula end)
  4. stirringstirred ambient for 16 hours
  5. additionsome primary amide product visible, further DMSO (0.1 ml) and 2M NaOH (0.2 ml) added
  6. stirringstirred ambient 16 hours
  7. customto give predominantly the acid
  8. customReaction products
  9. custompurified by Prep HPLC

Sources & evidence

ORD record
ord-cb79e675fc46492fbe3df92c1ee73396
Source dataset
uspto-grants-2015_09
Patent number
US09145354B2

Reaction notes

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