1,2-Dichloroethane → HCID 16112824, compound

HRID 551098Notes

Reaction equation

HRID 551098 reaction equation
[O:1]=[C:2]1[CH2:11][C:10]2([CH2:37][C:38]([OH:40])=O)[CH2:12][N:13]([CH2:14][C:15]3[CH:24]=[CH:23][C:22]4[C:17](=[CH:18][C:19]5[CH2:36][C@:26]6([C:34]7[C:29](=[N:30][CH:31]=[CH:32][CH:33]=7)[NH:28][C:27]6=[O:35])[CH2:25][C:20]=5[CH:21]=4)[N:16]=3)[C:8]3[C:9]2=[C:4]([CH:5]=[CH:6][CH:7]=3)[NH:3]1.[NH:41]1[CH2:45][CH2:44][CH2:43][CH2:42]1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.C(N(CC)C(C)C)(C)C>CN(C=O)C>[O:1]=[C:2]1[CH2:11][C:10]2([CH2:37][C:38](=[O:40])[N:41]3[CH2:45][CH2:44][CH2:43][CH2:42]3)[CH2:12][N:13]([CH2:14][C:15]3[CH:24]=[CH:23][C:22]4[C:17](=[CH:18][C:19]5[CH2:36][C@:26]6([C:34]7[C:29](=[N:30][CH:31]=[CH:32][CH:33]=7)[NH:28][C:27]6=[O:35])[CH2:25][C:20]=5[CH:21]=4)[N:16]=3)[C:8]3[C:9]2=[C:4]([CH:5]=[CH:6][CH:7]=3)[NH:3]1

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 31268PyrrolidineHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 57663771HCID 57663771, compound

Product 1

HCID 16112824HCID 16112824, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of [4-oxo-1-{[(7S)-2′-oxo-1′,2′,6,8-tetrahydrospiro[cyclopenta[g]quinoline-7,3′-pyrrolo[2,3-b]pyridin]-2-yl]methyl}-1,2,4,5-tetrahydropyrrolo[4,3,2-de]quinolin-2a(3H)-yl]acetic acid, diastereomer A (50 mg, 0.094 mmol, described in Example 2), pyrrolidine (20 mg, 0.282 mmol), EDC (22 mg, 0.113 mmol), HOBT (17 mg, 0.113 mmol), and N,N-diisopropylethylamine (0.082 mL, 0.470 mmol) was stirred in DMF (0.5 mL) at ambient temperature for 18 h. The reaction mixture was partitioned between saturated aqueous NaHCO3 (20 mL) and CH2Cl2 (10 mL). The organic layer was removed and the aqueous layer was extracted further with CH2Cl2 (2×10 mL). The combined organic extracts were washed with brine (10 mL), dried over Na2SO4, filtered, and concentrated in vacuo. The crude product was purified by silica gel chromatography, eluting with a gradient of CH2Cl2:MeOH—100:0 to 95:5, to give the title compound. MS: m/z=585 (M+1). HRMS: m/z=585.2620; calculated m/z=585.2609 for C35H33N6O3.

Workup

  1. customThe reaction mixture was partitioned between saturated aqueous NaHCO3 (20 mL) and CH2Cl2 (10 mL)
  2. customThe organic layer was removed
  3. extractionthe aqueous layer was extracted further with CH2Cl2 (2×10 mL)
  4. washThe combined organic extracts were washed with brine (10 mL)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude product was purified by silica gel chromatography
  9. washeluting with a gradient of CH2Cl2

Sources & evidence

ORD record
ord-28c9046e512d4b039d90b8a591d98500
Source dataset
uspto-grants-2011_05
Patent number
US07947677B2

Reaction notes

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