Ethanol → HCID 67809643, compound

HRID 1463909Notes

Reaction equation

HRID 1463909 reaction equation
C([O:3][C:4](=[O:55])[C:5]1[CH:10]=[C:9]([CH2:11][CH2:12][C:13]2[S:22][C:21]3[N:20]4[C:23]([CH3:26])=[N:24][N:25]=[C:19]4[CH2:18][N:17]=[C:16]([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=4[Cl:33])[C:15]=3[CH:14]=2)[CH:8]=[CH:7][C:6]=1[CH2:34][C:35]([NH:37][C:38]1[CH:43]=[CH:42][CH:41]=[C:40](/[CH:44]=[CH:45]/[C:46]2[S:47][CH:48]=[C:49]([CH:51]3[CH2:54][CH2:53][CH2:52]3)[N:50]=2)[CH:39]=1)=[O:36])C.[OH-].[Na+].O.C(O)C>C(O)(=O)C>[OH2:3].[Cl:33][C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=1[C:16]1[C:15]2[CH:14]=[C:13]([CH2:12][CH2:11][C:9]3[CH:8]=[CH:7][C:6]([CH2:34][C:35]([NH:37][C:38]4[CH:43]=[CH:42][CH:41]=[C:40](/[CH:44]=[CH:45]/[C:46]5[S:47][CH:48]=[C:49]([CH:51]6[CH2:54][CH2:53][CH2:52]6)[N:50]=5)[CH:39]=4)=[O:36])=[C:5]([CH:10]=3)[C:4]([OH:55])=[O:3])[S:22][C:21]=2[N:20]2[C:23]([CH3:26])=[N:24][N:25]=[C:19]2[CH2:18][N:17]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 962WaterHCID 14798Sodium HydroxideHCID 67807695HCID 67807695, compound

Product 1

HCID 67809643HCID 67809643, compoundYield 123.5%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 0.2 g (0.25 mmol) of (E)-5-[2-[4-(2-chlorophenyl)-9-methyl-6H-thieno-[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepin-2-yl]ethyl]-2-[2-[3-[2-(4-cyclobutyl-2-thiazolyl)ethenyl]phenylamino]-2-oxoethyl]-benzoic acid ethyl ester, 4 mL of 1N NaOH, 11 mL of H2O, and 15 mL of ethanol was stirred for 40 hours and acidified with acetic acid. The product was extracted with CH2Cl2, which was dried and concentrated. The residue was chromatographed on silica gel using ethyl acetate/ethanol (10:1) followed by the same mixture (4:1) as the eluent. The fractions containing the product were concentrated and the residue triturated with ether/pet. ether and filtered to give 0.12 g (61%) of (E)-5-[2-[4-(2-chlorophenyl)-9-methyl-6H-thieno-[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepin-2-yl]ethyl]-2-[2-[3-[2-(4-cyclobutyl-2-thiazolyl)ethenyl]phenylamino]-2-oxoethyl]-benzoic acid monohydrate as an off-white powder: mp 143°-148° C.

Workup

  1. extractionThe product was extracted with CH2Cl2, which
  2. customwas dried
  3. concentrationconcentrated
  4. customThe residue was chromatographed on silica gel
  5. additionThe fractions containing the product
  6. concentrationwere concentrated
  7. customthe residue triturated with ether/pet. ether
  8. filtrationfiltered

Sources & evidence

ORD record
ord-5cc0a7a07d774c68871ee5d51e7a79d7
Source dataset
uspto-grants-1994_04
Patent number
US05302590

Reaction notes

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