Carbon Tetrachloride → HCID 58137765, compound

HRID 2189459Notes

Reaction equation

HRID 2189459 reaction equation
[Cl:1][C:2]1[CH:28]=[CH:27][C:5]2[N:6]=[C:7]([NH:9][C:10]3[CH:26]=[CH:25][C:13]([C:14]([NH:16][NH:17][C:18]4[C:23]([Cl:24])=[N:22][CH:21]=[CH:20][N:19]=4)=O)=[CH:12][CH:11]=3)[S:8][C:4]=2[CH:3]=1.C(Cl)(Cl)(Cl)Cl.CCN(C(C)C)C(C)C.C(P(CC)CC)C>C(Cl)Cl.C1COCC1>[Cl:1][C:2]1[CH:28]=[CH:27][C:5]2[N:6]=[C:7]([NH:9][C:10]3[CH:26]=[CH:25][C:13]([C:14]4[N:19]5[CH:20]=[CH:21][N:22]=[C:23]([Cl:24])[C:18]5=[N:17][N:16]=4)=[CH:12][CH:11]=3)[S:8][C:4]=2[CH:3]=1

Participants

7

Reactant 4

HCID 5943Carbon TetrachlorideHCID 27365TriethylphosphineHCID 81531DiisopropylethylamineHCID 86650852HCID 86650852, compound

Product 1

HCID 58137765HCID 58137765, compoundYield 66.3%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 4-(6-chlorobenzo[d]thiazol-2-ylamino)-N′-(3-chloropyrazin-2-yl)benzohydrazide (63B) (6.17 g, 14.31 mmol) in a mixed solvent of CCl4 (60 mL), THF (80 mL) and CH2Cl2 (120 mL) cooled to 0° C. under argon was added DIPEA (18.49 g, 143 mmol), followed by dropwise addition of triethylphosphine (8.45 g, 71.5 mmol). After addition, the reaction mixture was stirred at 0° C. for 1 h, and then quenched by addition of water (100 mL). The precipitate was isolated by filtration and air dried to yield the first crop of the title compound as a dark brown solid (3.92 g). The filtrate was extracted with ethyl acetate (2×). The combined organics were washed with water (1×100 mL), dried over anhydrous Na2SO4 and concentrated in vacuo. The obtained residue was triturated with CH3OH/CH2Cl2 (35 mL/5 mL) to yield the second crop of the title compound (0.95 g) (total 4.87 g, 82% yield). HPLC/MS (Method C): retention time=2.61 min, [M+H]+=413.3. 1H NMR (500 MHz, DMSO-d6): δ 10.98 (s, 1H), 8.68 (d, J=4.95 Hz, 1H), 8.05 (d, J=8.25 Hz, 2H), 7.98 (s, 1H), 7.96 (d, J=825 Hz, 2H), 7.77 (d, J=4.95 Hz, 1H), 7.63 (d, J=8.25 Hz, 1H), 7.37 (d, J=8.80 Hz, 1H).

Workup

  1. additionAfter addition
  2. customquenched by addition of water (100 mL)
  3. customThe precipitate was isolated by filtration and air
  4. customdried

Sources & evidence

ORD record
ord-8b4d273074044d448e2c738a638895e4
Source dataset
uspto-grants-2012_12
Patent number
US08324241B2

Reaction notes

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