1,2-Dichloroethane → HCID 59316740, compound

HRID 2189788Notes

Reaction equation

HRID 2189788 reaction equation
ONC(=N)C1C2C(C=CC=1)=NN(CCCC(OCC)=O)C=2.[OH:22][NH:23][C:24](=[NH:42])[C:25]1[CH:33]=[CH:32][CH:31]=[C:30]2[C:26]=1[CH:27]=[N:28][N:29]2[CH2:34][CH2:35][CH2:36][C:37]([O:39][CH2:40][CH3:41])=[O:38].[Cl:43][C:44]1[CH:45]=[C:46]([CH:50]=[CH:51][C:52]=1[O:53][CH:54]([CH3:56])[CH3:55])[C:47](O)=O.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1>CN(C=O)C.CCOC(C)=O>[Cl:43][C:44]1[CH:45]=[C:46]([C:47]2[O:22][N:23]=[C:24]([C:25]3[CH:33]=[CH:32][CH:31]=[C:30]4[C:26]=3[CH:27]=[N:28][N:29]4[CH2:34][CH2:35][CH2:36][C:37]([O:39][CH2:40][CH3:41])=[O:38])[N:42]=2)[CH:50]=[CH:51][C:52]=1[O:53][CH:54]([CH3:55])[CH3:56]

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 225977283-Chloro-4-(propan-2-yloxy)benzoic acidHCID 178471587HCID 178471587, compoundHCID 178471593HCID 178471593, compound

Product 1

HCID 59316740HCID 59316740, compoundYield 23.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of a mixture of ethyl 4-{4-[(hydroxyamino)(imino)methyl]-2H-indazol-2-yl}butanoate & ethyl 4-{4-[(hydroxyamino)(imino)methyl]-1H-indazol-1-yl}butanoat (D56) (4 g, 13.78 mmol), 3-chloro-4-[(1-methylethyl)oxy]benzoic acid (D3) (2.96 g, 13.78 mmol), EDC (2.91 g, 15.16 mmol) and HOBT (2.321 g, 15.16 mmol) in DMF (40 ml) was stirred at RT for 3 hrs to form intermediate then heated at 120° C. for 2 hrs to cyclise. The solution was cooled, diluted with EtOAc, washed with water 3× dried (magnesium sulphate) and evaporated. Purified by flash chromatography eluting with EtOAc/iso-hexane 1:3. The combined fractions were evaporated to give the title compound (1.5 g) as a white solid. MS (ES): C24H2535ClN4O4 requires 468; found (MH+) 469. δH (CDCl3, 400 MHz): 1.24 (3H, t), 1.46 (6H, d), 2.31 (4H, m), 4.12 (2H, q), 4.55 (2H, t), 4.73 (1H, m), 7.08 (1H, d), 7.52 (1H, dd), 7.62 (1H, d), 8.06 (1H, dd), 8.10 (1H, dd), 8.29 (1H, d), 8.70 (1H, d).

Workup

  1. customto form intermediate
  2. temperaturethen heated at 120° C. for 2 hrs
  3. temperatureThe solution was cooled
  4. washwashed with water 3×
  5. dry with materialdried (magnesium sulphate)
  6. customevaporated
  7. customPurified by flash chromatography
  8. washeluting with EtOAc/iso-hexane 1:3
  9. customThe combined fractions were evaporated

Sources & evidence

ORD record
ord-d394c2146d3344969e8b1b3c031f16dc
Source dataset
uspto-grants-2012_12
Patent number
US08324254B2

Reaction notes

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