Thionyl Chloride → HCID 53309971, compound

HRID 1987119Notes

Reaction equation

HRID 1987119 reaction equation
O[CH:2]1[C:12]2[C:7](=[N:8][CH:9]=[C:10]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH:11]=2)[CH:6]=[CH:5][C:4]2[CH:19]=[CH:20][C:21]([NH:23][S:24]([CH3:27])(=[O:26])=[O:25])=[CH:22][C:3]1=2.O=S(Cl)Cl.[NH:32]1[CH2:36][CH2:35][CH2:34][CH2:33]1>C(Cl)Cl>[C:13]1([C:10]2[CH:11]=[C:12]3[CH:2]([N:32]4[CH2:36][CH2:35][CH2:34][CH2:33]4)[C:3]4[CH:22]=[C:21]([NH:23][S:24]([CH3:27])(=[O:25])=[O:26])[CH:20]=[CH:19][C:4]=4[CH:5]=[CH:6][C:7]3=[N:8][CH:9]=2)[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 31268PyrrolidineHCID 53309969HCID 53309969, compound

Product 1

HCID 53309971HCID 53309971, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a stirred solution of N-(5-hydroxy-3-phenyl-5H-benzo[4,5]cyclohepta[1,2-b]pyridin-7-yl)methanesulfonamide (40 mg, 0.11 mmol) in CH2Cl2 (2 mL) was added SOCl2 (30 uL, 0.41 mmol) at 0° C. The mixture was left to stir at 0° C. for 1 h and concentrated in vacuo. To the residue were added CH2Cl2 (2 mL) and pyrroldine (0.10 mL, 1.2 mmol) at 0° C. The mixture was allowed to warm to room temperature as the bath did, and left to stir overnight. The mixture was concentrated and purified by flash chromatography to afford the title compound. 1H NMR (600 MHz, CD3OD) δ 8.83 (s, 1EI); 7.91 (s, 1H); 7.15-7.64 (m, 10H); 4.31 (br s, 1H); 3.02 (s, 3H); 2.09 (br s, 4H); 1.61 (br s, 4H). LRMS (APCI) calc'd for (C25H26N3O2S) [M+H]+, 432.2; found 432.1.

Workup

  1. waitThe mixture was left
  2. concentrationconcentrated in vacuo
  3. temperatureto warm to room temperature as the bath
  4. waitleft
  5. stirringto stir overnight
  6. concentrationThe mixture was concentrated
  7. custompurified by flash chromatography

Sources & evidence

ORD record
ord-3620eae7ac8e45c6aad019c7e2157e35
Source dataset
uspto-grants-2009_06
Patent number
US07550478B2

Reaction notes

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