Triethylamine → HCID 22594965, compound

HRID 1263390Notes

Reaction equation

HRID 1263390 reaction equation
Cl[C:2](Cl)([O:4]C(=O)OC(Cl)(Cl)Cl)Cl.[NH2:13][C:14]1[CH:15]=[C:16]([C:20]2[C:24]([Br:25])=[CH:23][N:22]([CH3:26])[N:21]=2)[CH:17]=[CH:18][CH:19]=1.C(N(CC)CC)C.[F:34][C:35]([F:46])([F:45])[O:36][C:37]1[CH:44]=[CH:43][C:40]([CH2:41][NH2:42])=[CH:39][CH:38]=1>C(Cl)Cl>[Br:25][C:24]1[C:20]([C:16]2[CH:15]=[C:14]([NH:13][C:2]([NH:42][CH2:41][C:40]3[CH:43]=[CH:44][C:37]([O:36][C:35]([F:45])([F:46])[F:34])=[CH:38][CH:39]=3)=[O:4])[CH:19]=[CH:18][CH:17]=2)=[N:21][N:22]([CH3:26])[CH:23]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 94429TriphosgeneHCID 5718464-(Trifluoromethoxy)benzylamineHCID 27353913-(4-Bromo-1-Methyl-1H-Pyrazol-3-Yl)Aniline

Product 1

HCID 22594965HCID 22594965, compoundYield 202.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of triphosgene (12 mg, 0.04 mmol) in CH2Cl2 (0.5 mL) was added dropwise a solution of 3-(3-aminophenyl)4-bromo-1-methylpyrazole (30 mg, 0.12 mmol) and triethylamine (33 μL, 0.24 mmol) in CH2Cl2 (0.5 mL). After 1 h, 4-(trifluoromethoxy)benzylamine (23 mg, 0.12 mmol) was added. The reaction mixture was stirred for 16 h and concentrated. Chromatography on flash silica (75% EtOAc/hexane) gave the title compound as a colourless solid (38 mg, 68%), m.p. 144.6-145.8° C. (EtOAc/hexane).

Workup

  1. concentrationconcentrated

Sources & evidence

ORD record
ord-1e083b1912e64e0aafd7e1ea671dbe0b
Source dataset
uspto-grants-2003_04
Patent number
US06541209B1

Reaction notes

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