L-Lactic Acid → HCID 178462374, compound

HRID 2036253Notes

Reaction equation

HRID 2036253 reaction equation
[NH2:1][C:2]1[CH:33]=[C:32]([NH2:34])[C:31]([Cl:35])=[CH:30][C:3]=1[C:4]([NH:6][C:7](=[NH:29])[NH:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:16]([O:23][CH2:24][CH:25]([OH:28])[CH2:26][OH:27])=[CH:15][CH:14]=1)=[O:5].[C:36]([OH:41])(=[O:40])[C@H:37]([CH3:39])[OH:38]>CCO>[C:36]([OH:41])(=[O:40])[CH:37]([CH3:39])[OH:38].[C:36]([OH:41])(=[O:40])[C@H:37]([CH3:39])[OH:38].[NH2:1][C:2]1[CH:33]=[C:32]([NH2:34])[C:31]([Cl:35])=[CH:30][C:3]=1[C:4]([NH:6][C:7](=[NH:29])[NH:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:16]([O:23][CH2:24][CH:25]([OH:28])[CH2:26][OH:27])=[CH:15][CH:14]=1)=[O:5]

Participants

5

Reactant 2

HCID 107689L-Lactic AcidHCID 178512153HCID 178512153, compound

Product 2

HCID 612Lactic AcidHCID 178462374HCID 178462374, compoundYield 158.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 2,4-diamino-5-chloro-N—(N-{4-[4-(2,3-dihydroxypropoxy)naphthalen-1-yl]butyl}carbamimidoyl)benzamide (24, 28 mg, 0.06 mmole) in EtOH (10 mL) was added L-(+)-lactic acid (5.20 mg, 0.06 mmole) at room temperature and the reaction mixture was stirred for 15 min. The solution was concentrated and the residue was azeotroped with MeOH. The residue was dissolved in H2O (3 mL) and lyophilized to afford lactic acid salt 26 (28 mg, 84%) as a yellow solid: mp 115-118° C.; 1H NMR (300 MHz, CD3OD) δ 8.32 (d, J=8.4 Hz, 1H), 8.01 (d, J=8.4 Hz, 1H), 7.53-7.40 (m, 2H), 7.24 (d, J=7.8 Hz, 1H), 6.83 (d, J=7.8 Hz, 1H), 4.21-4.10 (m, 3H), 4.01-3.94 (m, 1H), 3.82-3.73 (m, 2H), 3.35-3.33 (m, 2H), 3.08 (t, J=7.0, Hz, 1H), 1.89-1.77 (m, 4H), 1.31 (d, J=7.0 Hz, 3H); ESI-MS m/z 524 [C23H28ClN7O4+H]+.

Workup

  1. concentrationThe solution was concentrated
  2. customthe residue was azeotroped with MeOH
  3. dissolutionThe residue was dissolved in H2O (3 mL)

Sources & evidence

ORD record
ord-5be636df4dd8416c8ea605776ef91c2f
Source dataset
uspto-grants-2013_11
Patent number
US08575176B2

Reaction notes

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