Thionyl Chloride → HCID 53309971, compound

HRID 222292Notes

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

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 pyrrolidine (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, 1H); 7.91 (s, 1H); 7.15-7.64 (m, 10); 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

waitThe mixture was left
concentrationconcentrated in vacuo
temperatureto warm to room temperature as the bath
waitleft
stirringto stir overnight
concentrationThe mixture was concentrated
custompurified by flash chromatography

Sources & evidence

ORD record: ord-d4b0d0cea2c846779620abbd8d5d10a5
Source dataset: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08207186B2

Reaction notes

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