1,2-Dichloroethane → HCID 67436193, compound

HRID 1663414Notes

Reaction equation

HRID 1663414 reaction equation
C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl.CCN(C(C)C)C(C)C.[O:24]=[C:25]1[C:34]2[CH:35]=[N:36][C:37]([C:39]3[CH:47]=[CH:46][C:42]([C:43](O)=[O:44])=[CH:41][CH:40]=3)=[CH:38][C:33]=2[O:32][C:31]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]1=2.[NH:48]1[CH2:53][CH2:52][O:51][CH2:50][CH2:49]1>CN(C=O)C.C(Cl)Cl>[N:48]1([C:43]([C:42]2[CH:41]=[CH:40][C:39]([C:37]3[N:36]=[CH:35][C:34]4[C:25](=[O:24])[C:26]5[CH:27]=[CH:28][CH:29]=[CH:30][C:31]=5[O:32][C:33]=4[CH:38]=3)=[CH:47][CH:46]=2)=[O:44])[CH2:53][CH2:52][O:51][CH2:50][CH2:49]1

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 8083MorpholineHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 67436976HCID 67436976, compound

Product 1

HCID 67436193HCID 67436193, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

HOBt (145 mg, 0.945 mmol), EDC (181 mg, 0.945 mmol) and Hunig's base (0.550 mL, 3.15 mmol) were added to a suspension of 4-(10-oxo-10H-chromeno[3,2-c]pyridin-3-yl)benzoic acid (200 mg, 0.630 mmol) in DMF (15 mL) and CH2Cl2 (10 mL) at room temperature. After 5 min, morpholine (0.110 mL, 1.261 mmol) was added. After 13 h at rt, the mixture was quenched with saturated NH4Cl (50 mL) and extracted with CH2Cl2 (3×50 mL). The combined extracts were dried (MgSO4) and concentrated to give crude 3-(4-(morpholine-4-carbonyl)phenyl)-10H-chromeno[3,2-c]pyridin-10-one, which was taken to next reaction without purification. MS (ES+) m/z: 387 (M+H).

Workup

  1. waitAfter 13 h at rt
  2. customthe mixture was quenched with saturated NH4Cl (50 mL)
  3. extractionextracted with CH2Cl2 (3×50 mL)
  4. dry with materialThe combined extracts were dried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-4d1c9ef602b14dcc87b8e8ff90492bc1
Source dataset
uspto-grants-2011_10
Patent number
US08034940B2

Reaction notes

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