Acetic Acid → HCID 136385313, compound

HRID 1467689Notes

Reaction equation

HRID 1467689 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[C:13]3=[N:14][NH:15][C:16](=[O:21])[C:17]4[CH:18]=[CH:19][CH:20]=[C:11]([C:12]=43)[NH:10][CH:9]2[C:22]2[CH:29]=[CH:28][C:25]([CH:26]=O)=[CH:24][CH:23]=2)=[CH:4][CH:3]=1.CC(O)=O.[NH:34]1[CH2:38][CH2:37][CH2:36][CH2:35]1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].Cl>C(Cl)Cl.C(OCC)(=O)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[C:13]3=[N:14][NH:15][C:16](=[O:21])[C:17]4[CH:18]=[CH:19][CH:20]=[C:11]([C:12]=43)[NH:10][CH:9]2[C:22]2[CH:23]=[CH:24][C:25]([CH2:26][N:34]3[CH2:38][CH2:37][CH2:36][CH2:35]3)=[CH:28][CH:29]=2)=[CH:4][CH:3]=1

Participants

8

Reactant 5

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 31268PyrrolidineHCID 5049666Sodium triacetoxyborohydrideHCID 136344749HCID 136344749, compound

Product 1

HCID 136385313HCID 136385313, compoundYield 26.2%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred mixture of 4-(9-(4-fluorophenyl)-3-oxo-3,7,8,9-tetrahydro-2H-pyrido[4,3,2-de]phthalazin-8-yl)benzaldehyde (0.1 g, 0.26 mmol) in anhydrous DCM (4 mL) was added AcOH (94 mg, 1.56 mmol) at 25° C. for 0.5 h, then pyrrolidine (37 mg, 0.52 mmol) was added at 25° C., stirred overnight. NaBH(OAc)3 was added at ice bath, and stirred for 5 h. The mixture was concentrated to give the crude product. The crude product was dissolved in ethyl acetate and to this solution was added 2N HCl (10 mL). The aqueous phase was separated and 20% NaOH (20 ml) was added. The mixture was extracted with ethyl acetate and the organic phase was separated to give the title compound (30 mg, yield 26%). LC-MS (ESI) m/z: 441 (M+1)+.

Workup

  1. stirringstirred for 5 h
  2. concentrationThe mixture was concentrated
  3. customto give the crude product
  4. customThe aqueous phase was separated
  5. addition20% NaOH (20 ml) was added
  6. extractionThe mixture was extracted with ethyl acetate
  7. customthe organic phase was separated

Sources & evidence

ORD record
ord-57aebbbec0c34bfa9a3f4896ccf95ded
Source dataset
uspto-grants-2015_04
Patent number
US08999987B2

Reaction notes

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