Thionyl Chloride → HCID 58550614, compound

HRID 1890702Notes

Reaction equation

HRID 1890702 reaction equation
O[CH2:2][C:3]1[CH:4]=[N:5][C:6]2[C:11]([CH:12]=1)=[CH:10][C:9]1[CH2:13][C@:14]3([CH2:24][C:8]=1[CH:7]=2)[C:22]1[C:17](=[N:18][CH:19]=[CH:20][CH:21]=1)[NH:16][C:15]3=[O:23].S(Cl)([Cl:27])=O>C(Cl)Cl>[Cl:27][CH2:2][C:3]1[CH:4]=[N:5][C:6]2[C:11]([CH:12]=1)=[CH:10][C:9]1[CH2:13][C@:14]3([CH2:24][C:8]=1[CH:7]=2)[C:22]1[C:17](=[N:18][CH:19]=[CH:20][CH:21]=1)[NH:16][C:15]3=[O:23]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 58550612(3′S)-6,8-Dihydro-3-(hydroxymethyl)spiro[7H-cyclopenta[g]quinoline-7,3′-[3H]pyrrolo[2,3-b]pyridin]-2′(1′H)-one

Product 1

HCID 58550614HCID 58550614, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of (7S)-3-(hydroxymethyl)-6,8-dihydrospiro[cyclopenta[g]quinoline-7,3′-pyrrolo[2,3-b]pyridin]-2′(1′H)-one from Step A (970 mg, 3.06 mmol) in CH2Cl2 (30 mL) was added thionyl chloride (2.23 mL, 30.1 mmol) and the resulting mixture was stirred at ambient temperature for 2 h, then concentrated in vacuo. The residue was partitioned between saturated aqueous NaHCO3 (30 mL) and CH2Cl2 (30 mL). The layers were separated and the aqueous layer was extracted further with CH2Cl2 (2×30 mL). The combined organic extracts were dried over Na2SO4, filtered, and concentrated in vacuo to give the title. MS: m/z=336 (M+1).

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was partitioned between saturated aqueous NaHCO3 (30 mL) and CH2Cl2 (30 mL)
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted further with CH2Cl2 (2×30 mL)
  5. dry with materialThe combined organic extracts were dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto give the title

Sources & evidence

ORD record
ord-4386b42c916040f3b571c5841e575b28
Source dataset
uspto-grants-2013_08
Patent number
US08507477B2

Reaction notes

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