Hexachloroethane → HCID 60198273, compound

HRID 2279446Notes

Reaction equation

HRID 2279446 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([NH:15][C:16]([N:18]2[CH2:27][CH2:26][C:25]3[CH:24]=[N:23][C:22]([NH:28][CH:29]4[CH2:34][CH2:33][O:32][CH2:31][CH2:30]4)=[N:21][C:20]=3[CH2:19]2)=[O:17])[C:9]([NH:11][NH:12][CH:13]=O)=[O:10])=[CH:4][C:3]=1[F:35].CCN(C(C)C)C(C)C.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.ClC(Cl)(Cl)C(Cl)(Cl)Cl>CC#N>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:9]2[O:10][CH:13]=[N:12][N:11]=2)[NH:15][C:16]([N:18]2[CH2:27][CH2:26][C:25]3[CH:24]=[N:23][C:22]([NH:28][CH:29]4[CH2:34][CH2:33][O:32][CH2:31][CH2:30]4)=[N:21][C:20]=3[CH2:19]2)=[O:17])=[CH:4][C:3]=1[F:35]

Participants

6

Reactant 4

HCID 6214HexachloroethaneHCID 11776TriphenylphosphineHCID 81531DiisopropylethylamineHCID 86705472HCID 86705472, compound

Product 1

HCID 60198273HCID 60198273, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 48 (119 mg, 0.212 mmol) and MeCN (2 mL) was added DIPEA (164 mg, 1.27 mmol) and PPh3 (99.9 mg, 0.381 mmol) and the solution was stirred for 5 min. Perchloroethane (65.1 mg, 0.275 mmol) was added and the reaction was stirred for 3 h. The reaction mixture was concentrated and partitioned between EtOAc and H2O. The organic layer was separated and the aqueous phase was extracted with EtOAc. The organic layers were combined and concentrated. The crude product was purified by reverse phase chromatography (SP4) eluting with a MeCN/H2O gradient (5-95% MeCN) to afford 50.0 mg (48.4%) of I-9: 1H NMR (400 MHz, CDCl3) δ 8.39 (s, 1H), 8.08 (s, 1H), 7.41 (t, 1H), 7.21 (dd, 1H), 7.14 (d, 1H), 6.35 (d, 1H), 5.83 (d, 1H), 4.90 (d, 1H), 4.43 (s, 2H), 4.05-3.95 (m, 3H), 3.77-3.60 (m, 2H), 3.55 (t, 2H), 2.70 (m, 2H), 2.03 (d, 2H), 1.53 (m, 2H); LCMS (ACPI-pos) m/z 488.2 (M+H)+.

Workup

  1. stirringthe reaction was stirred for 3 h
  2. concentrationThe reaction mixture was concentrated
  3. custompartitioned between EtOAc and H2O
  4. customThe organic layer was separated
  5. extractionthe aqueous phase was extracted with EtOAc
  6. concentrationconcentrated
  7. customThe crude product was purified by reverse phase chromatography (SP4)
  8. washeluting with a MeCN/H2O gradient (5-95% MeCN)
  9. customto afford 50.0 mg (48.4%) of I-9: 1H NMR (400 MHz, CDCl3) δ 8.39 (s, 1H), 8.08 (s, 1H), 7.41 (t, 1H), 7.21 (dd, 1H), 7.14 (d, 1H), 6.35 (d, 1H), 5.83 (d, 1H), 4.90 (d, 1H), 4.43 (s, 2H), 4.05-3.95 (m, 3H), 3.77-3.60 (m, 2H), 3.55 (t, 2H), 2.70 (m, 2H), 2.03 (d, 2H), 1.53 (m, 2H)

Sources & evidence

ORD record
ord-bf6ba9986a47413f88457ae96168c965
Source dataset
uspto-grants-2015_09
Patent number
US09133187B2

Reaction notes

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