Triethylamine → HCID 67265469, compound

HRID 1685928Notes

Reaction equation

HRID 1685928 reaction equation
Cl.[NH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([NH:12][C:13](=[O:22])[C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([O:20][CH3:21])[CH:15]=2)=[CH:8][C:7]=1[C:23]1[N:27]([CH3:28])[N:26]=[CH:25][CH:24]=1.C(N(CC)CC)C.[Cl:36][C:37]([Cl:47])([O:39][C:40](=O)[O:41]C(Cl)(Cl)Cl)[Cl:38]>ClCCl>[CH3:21][O:20][C:16]1[CH:15]=[C:14]([CH:19]=[CH:18][CH:17]=1)[C:13]([NH:12][C:9]1[CH:10]=[CH:11][C:6]([O:5][CH2:4][CH2:3][NH:2][C:40](=[O:41])[O:39][C:37]([Cl:47])([Cl:38])[Cl:36])=[C:7]([C:23]2[N:27]([CH3:28])[N:26]=[CH:25][CH:24]=2)[CH:8]=1)=[O:22]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 94429TriphosgeneHCID 67265457N-(4-(2-aminoethoxy)-3-(1-methyl-1H-pyrazol-5-yl)phenyl)-3-methoxybenzamide hydrochloride

Product 1

HCID 67265469HCID 67265469, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-(4-(2-aminoethoxy)-3-(1-methyl-1H-pyrazol-5-yl)phenyl)-3-methoxybenzamide hydrochloride (80.0 mg, 1981 mmol), triethylamine (277 μl, 10 eq) and triphosgene (64.8 mg, 1.1 eq) were dissolved in 5 mL of dichloromethane and stirred under reflux for 5 mins. The solvent was removed under vacuum and 4 mL of ethyl acetate was added. It was divided in two and used immediately in the preparation of compound 5 and 7 without purification. LCMS m/z (%)=528 (M+H, 100).

Workup

  1. temperatureunder reflux for 5 mins
  2. customThe solvent was removed under vacuum and 4 mL of ethyl acetate
  3. additionwas added
  4. customused immediately in the preparation of compound 5 and 7 without purification

Sources & evidence

ORD record
ord-6f18665ffd814b349dd528e27d61ec3b
Source dataset
uspto-grants-2012_04
Patent number
US08148417B2

Reaction notes

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