Diisopropylethylamine → HCID 67440451, compound

HRID 1400866Notes

Reaction equation

HRID 1400866 reaction equation
[C:1]([O:4][CH2:5][C:6]([N:8]([CH2:13][C:14]1[N:18]([CH3:19])[C:17]([C:20]2[S:28][C:27]3[C:22](=[N:23][CH:24]=[CH:25][C:26]=3[O:29][C:30]3[CH:35]=[CH:34][C:33]([NH2:36])=[CH:32][C:31]=3[F:37])[CH:21]=2)=[N:16][CH:15]=1)[CH2:9][CH2:10][O:11][CH3:12])=[O:7])(=[O:3])[CH3:2].CC[N:40]([CH:44](C)C)[CH:41]([CH3:43])[CH3:42].ClC(Cl)([O:50]C(=O)OC(Cl)(Cl)Cl)Cl>C1COCC1>[C:1]([O:4][CH2:5][C:6]([N:8]([CH2:13][C:14]1[N:18]([CH3:19])[C:17]([C:20]2[S:28][C:27]3[C:22](=[N:23][CH:24]=[CH:25][C:26]=3[O:29][C:30]3[CH:35]=[CH:34][C:33]([NH:36][C:44]([NH:40][CH:41]4[CH2:42][CH2:43]4)=[O:50])=[CH:32][C:31]=3[F:37])[CH:21]=2)=[N:16][CH:15]=1)[CH2:9][CH2:10][O:11][CH3:12])=[O:7])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 94429TriphosgeneHCID 58474538HCID 58474538, compound

Product 1

HCID 67440451HCID 67440451, compoundYield 114.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 207 (130 mg, 0.246 mmol) in THF (20 mL) at 0° C. was added. DIPEA (0.172 mL, 0.986 mmol) and triphosgene (43.9 mg, 0.148 mmol). The reaction mixture was stirred for 1 hr at 0° C. before cyclopylamine (70.3 mg, 1.232 mmol) was added. The reaction mixture was allowed to warm up to room temperature and stirred for 1 hr before concentration. The residue was purified by Biotage (MeO/DCM, 0-20%, SNAP 25 g cartridge) to give the title compound 208 (104 mg, 0.170 mmol, 69% yield) as a white solid. MS: 611 (MH)+.

Workup

  1. additionwas added
  2. temperatureto warm up to room temperature
  3. stirringstirred for 1 hr before concentration
  4. customThe residue was purified by Biotage (MeO/DCM, 0-20%, SNAP 25 g cartridge)

Sources & evidence

ORD record
ord-d0e84a268b544d588157cb834dbff63b
Source dataset
uspto-grants-2014_12
Patent number
US08906852B2

Reaction notes

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