Water → HCID 89620489, compound

HRID 1499994Notes

Reaction equation

HRID 1499994 reaction equation
[Cl:1][C:2]1[C:10]([C:11]2[CH2:15][CH:14]([CH2:16][C:17]#[N:18])[O:13][N:12]=2)=[C:9]([S:19]([CH2:22][CH3:23])(=[O:21])=[O:20])[CH:8]=[CH:7][C:3]=1[C:4](O)=[O:5].C([NH:27][C:28]1[N:32]([CH3:33])[N:31]=[N:30][N:29]=1)C=C.C(Cl)(=O)C(Cl)=O.O>N1C=CC=CC=1.ClC(Cl)C>[Cl:1][C:2]1[C:10]([C:11]2[CH2:15][CH:14]([CH2:16][C:17]#[N:18])[O:13][N:12]=2)=[C:9]([S:19]([CH2:22][CH3:23])(=[O:20])=[O:21])[CH:8]=[CH:7][C:3]=1[C:4]([NH:27][C:28]1[N:32]([CH3:33])[N:31]=[N:30][N:29]=1)=[O:5]

Participants

7

Reactant 4

HCID 962WaterHCID 65578Oxalyl chlorideHCID 54595140HCID 54595140, compoundHCID 67041496HCID 67041496, compound

Product 1

HCID 89620489HCID 89620489, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 63651,1-DichloroethaneSolvent

Conditions

Temperature
75 °C

Procedure

178 mg (0.5 mmol) of 2-chloro-3-[5-(cyanomethyl)-4,5-dihydro-1,2-oxazol-3-yl]-4-(ethylsulfonyl)benzoic acid and 90 mg (0.65 mmol) of N-allyl-1-methyl-1H-tetrazol-5-amine are stirred in 3 ml of pyridine at room temperature (RT) for 1 h, and then a solution of 86 mg (0.675 mmol) of oxalyl chloride in 2 ml of dichloroethane is added. Subsequently, the mixture is stirred at 75° C. for 4 h. After cooling to RT, 0.5 ml of water is added. Then the mixture is stirred at RT for 30 min. The reaction solution is filtered and concentrated. The residue is purified by means of preparative HPLC (acetonitrile/water). Yield: 19 mg (8%).

Workup

  1. temperatureAfter cooling to RT
  2. stirringThen the mixture is stirred at RT for 30 min
  3. filtrationThe reaction solution is filtered
  4. concentrationconcentrated
  5. customThe residue is purified by means of preparative HPLC (acetonitrile/water)

Sources & evidence

ORD record
ord-89b8ed821e2b408fbdc7fc12a3897719
Source dataset
uspto-grants-2015_12
Patent number
US09204650B2

Reaction notes

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