Maleic Acid → HCID 131725962, compound

HRID 1241607Notes

Reaction equation

HRID 1241607 reaction equation
[C:1]([OH:8])(=[O:7])/[CH:2]=[CH:3]\[C:4]([OH:6])=[O:5].[CH2:9]([N:11]([CH2:55][CH3:56])[CH2:12][CH2:13][N:14]([C:29]([CH2:31][N:32]1[CH:37]=[C:36]([CH2:38][C:39]2[CH:40]=[N:41][N:42]([CH3:44])[CH:43]=2)[C:35](=[O:45])[N:34]=[C:33]1[S:46][CH2:47][C:48]1[CH:53]=[CH:52][C:51]([F:54])=[CH:50][CH:49]=1)=[O:30])[CH2:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]2[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=2)=[CH:18][CH:17]=1)[CH3:10]>CO>[C:1]([OH:8])(=[O:7])/[CH:2]=[CH:3]\[C:4]([OH:6])=[O:5].[CH2:55]([N:11]([CH2:9][CH3:10])[CH2:12][CH2:13][N:14]([C:29]([CH2:31][N:32]1[CH:37]=[C:36]([CH2:38][C:39]2[CH:40]=[N:41][N:42]([CH3:44])[CH:43]=2)[C:35](=[O:45])[N:34]=[C:33]1[S:46][CH2:47][C:48]1[CH:53]=[CH:52][C:51]([F:54])=[CH:50][CH:49]=1)=[O:30])[CH2:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]2[CH:23]=[CH:24][C:25]([Cl:28])=[CH:26][CH:27]=2)=[CH:18][CH:17]=1)[CH3:56]

Participants

4

Reactant 2

HCID 444266Maleic AcidHCID 23395801HCID 23395801, compound

Product 1

HCID 131725962HCID 131725962, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A solution of maleic acid (0.58 g, 1 equiv) in methanol (10 ml) was added to a solution of the free base from Example 6 (3.43 g, 1 equiv) in methanol (10 ml) with stirring. The mixture was evaporated to ca. half volume, diluted with ether, then the supernatent decanted off. The oil was triturated with ether to obtain a solid, which was filtered off, washed with ether and dried in vacuo; yield 3.69 g. 1H-NMR (DMSO, ca. 3:1 rotamer mixture) essentially similar to Example 7, plus δ 2.33 (3H,s); MS (APCI+) found (M+1)=687/689; C37H40ClFN6O2S requires 686/688.

Workup

  1. customThe mixture was evaporated to ca. half volume
  2. additiondiluted with ether
  3. customthe supernatent decanted off
  4. customThe oil was triturated with ether
  5. customto obtain a solid, which
  6. filtrationwas filtered off
  7. washwashed with ether
  8. customdried in vacuo

Sources & evidence

ORD record
ord-ce0ea79d4d814ec8985b0cfb90df482e
Source dataset
uspto-grants-2006_10
Patent number
US07115616B2

Reaction notes

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