Thionyl Chloride → HCID 67442446, compound

HRID 1400813Notes

Reaction equation

HRID 1400813 reaction equation
[CH:1]1([NH:4][C:5]([NH:7][C:8]2[CH:13]=[CH:12][C:11]([O:14][C:15]3[CH:20]=[CH:19][N:18]=[C:17]4[CH:21]=[C:22]([C:24]5[CH:29]=[CH:28][C:27]([CH2:30]O)=[CH:26][N:25]=5)[S:23][C:16]=34)=[C:10]([F:32])[CH:9]=2)=[O:6])[CH2:3][CH2:2]1.O=S(Cl)[Cl:35]>>[Cl:35][CH2:30][C:27]1[CH:28]=[CH:29][C:24]([C:22]2[S:23][C:16]3[C:17](=[N:18][CH:19]=[CH:20][C:15]=3[O:14][C:11]3[CH:12]=[CH:13][C:8]([NH:7][C:5]([NH:4][CH:1]4[CH2:3][CH2:2]4)=[O:6])=[CH:9][C:10]=3[F:32])[CH:21]=2)=[N:25][CH:26]=1

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 67442607HCID 67442607, compound

Product 1

HCID 67442446HCID 67442446, compound

Procedure

Into a 500 mL round-bottom flask containing 64 (5.34 g, 11.85 mmol) was added slowly SOCl2 (30 mL, 411 mmol). The yellow solution was stirred at RT for 2 h and cooled to 0° C. The reaction mixture was quenched by addition of ice (150 g) and water (100 mL), and the yellow suspension was shaken at RT for 1 h. The solid was collected by filtration, rinsed with water and dried under high vacuum. The crude product was triturated with AcOEt to afford the title compound 65 (5.55 g, purity ˜40% by HPLC, contaminated with the des-cyclopropyl side-product) as a yellow solid. MS (m/z): 469.1 (M+H). The material was used in the next step with no additional purification.

Workup

  1. temperaturecooled to 0° C
  2. customThe reaction mixture was quenched by addition of ice (150 g) and water (100 mL)
  3. stirringthe yellow suspension was shaken at RT for 1 h
  4. filtrationThe solid was collected by filtration
  5. washrinsed with water
  6. customdried under high vacuum
  7. customThe crude product was triturated with AcOEt

Sources & evidence

ORD record
ord-f19fe2ff96884893a76d6f66faf9f364
Source dataset
uspto-grants-2014_12
Patent number
US08906852B2

Reaction notes

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