Triethylamine → HCID 57639703, compound

HRID 909207Notes

Reaction equation

HRID 909207 reaction equation
O=C1CCC(=O)N1O[C:9]([C:11]1[CH:19]=[C:18]2[C:14]([CH:15]=[N:16][N:17]2[CH2:20][CH:21]([CH3:23])[CH3:22])=[CH:13][C:12]=1[O:24][C:25]1[CH:30]=[CH:29][C:28]([F:31])=[CH:27][C:26]=1[F:32])=[O:10].Cl.Cl.[CH3:35][O:36][C:37](=[O:45])[CH:38]([NH2:44])[CH2:39][CH2:40][N:41]([CH3:43])[CH3:42].C(N(CC)CC)C>ClCCl>[CH3:35][O:36][C:37](=[O:45])[C@@H:38]([NH:44][C:9]([C:11]1[CH:19]=[C:18]2[C:14]([CH:15]=[N:16][N:17]2[CH2:20][CH:21]([CH3:23])[CH3:22])=[CH:13][C:12]=1[O:24][C:25]1[CH:30]=[CH:29][C:28]([F:31])=[CH:27][C:26]=1[F:32])=[O:10])[CH2:39][CH2:40][N:41]([CH3:43])[CH3:42]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 426324812,5-dioxopyrrolidin-1-yl 5-(2,4-difluorophenoxy)-1-isobutyl-1H-indazole-6-carboxylateHCID 57418767HCID 57418767, compound

Product 1

HCID 57639703HCID 57639703, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-(2,4-difluorophenoxy)-1-isobutyl-1H-indazole-6-carboxylic acid 2,5-dioxopyrrolidin-1-yl ester (32.0 g, 72.2 mmol) and 2-amino-4-dimethylaminobutyric acid methyl ester dihydrochloride (19.35 g, 83.0 mmol) in dichloromethane was added triethylamine (35 mL, 253 mmol) and the mixture stirred at room temperature for 4 hours. The reaction mixture was concentrated under reduced pressure and diluted with dichloromethane (400 mL). The solution was washed with saturated NH4Cl (2×200 mL), saturated NaHCO3 (2×200 mL) and brine (200 mL). The organics were dried over MgSO4 and concentrated under reduced pressure to afford the crude product.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additiondiluted with dichloromethane (400 mL)
  3. washThe solution was washed with saturated NH4Cl (2×200 mL), saturated NaHCO3 (2×200 mL) and brine (200 mL)
  4. dry with materialThe organics were dried over MgSO4
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-87b06249c6b64a3382830c0e7f204cb7
Source dataset
uspto-grants-2011_09
Patent number
US08017641B2

Reaction notes

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