Triethylamine → HCID 57555085, compound

HRID 1011933Notes

Reaction equation

HRID 1011933 reaction equation
Cl.[NH2:2][C:3]1[CH:4]=[C:5]([N:9]2[C:13]([CH3:14])=[C:12]([C:15]([N:17]3[CH2:22][CH2:21][CH:20]([N:23]4[CH2:27][CH2:26][CH2:25][CH2:24]4)[CH2:19][CH2:18]3)=[O:16])[C:11]([CH3:28])=[N:10]2)[CH:6]=[CH:7][CH:8]=1.C(N(CC)CC)C.[Cl:36][C:37]1[CH:38]=[C:39]([CH:43]=[CH:44][C:45]=1[Cl:46])[C:40](Cl)=[O:41]>C(Cl)Cl>[Cl:36][C:37]1[CH:38]=[C:39]([CH:43]=[CH:44][C:45]=1[Cl:46])[C:40]([NH:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([N:9]2[C:13]([CH3:14])=[C:12]([C:15]([N:17]3[CH2:22][CH2:21][CH:20]([N:23]4[CH2:24][CH2:25][CH2:26][CH2:27]4)[CH2:19][CH2:18]3)=[O:16])[C:11]([CH3:28])=[N:10]2)[CH:4]=1)=[O:41]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 76403Benzoyl chloride, 3,4-dichloro-HCID 67315202HCID 67315202, compound

Product 1

HCID 57555085HCID 57555085, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 0.080 g (0.20 mmol) of [1-(3-amino-phenyl)-3,5-dimethyl-1H-pyrazol-4-yl]-(4-pyrrolidin-1-yl-piperidin-1-yl)-methanone hydrochloride and 0.11 ml (0.79 mmol, 4 eq) of triethylamine in 3 ml of CH2Cl2 was treated at 0° C. with 0.050 g (0.24 mmol, 1.2 eq) of 3,4-dichlorobenzoyl chloride. The reaction was stirred over night at RT, then partitioned three times between EtOAc and aqueous saturated NaHCO3, dried over Na2SO4 and evaporated to give 0.115 g (quant.) of the title compound as light yellow solid. MS: 540.4 (MH+, 2 Cl).

Workup

  1. custompartitioned three times between EtOAc and aqueous saturated NaHCO3
  2. dry with materialdried over Na2SO4
  3. customevaporated

Sources & evidence

ORD record
ord-82de66425eb349919f2dca5f1ed6eea5
Source dataset
uspto-grants-2011_07
Patent number
US07977358B2

Reaction notes

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