Ammonium Acetate → HCID 136390211, compound

HRID 1046979Notes

Reaction equation

HRID 1046979 reaction equation
O=C(C[N:8]1C(=O)C2C=CC=CC=2NC2N=CC=CC1=2)CC([O-])=O.O=[C:25]([CH2:31][N:32]1[C:38](=O)[C:37]2[CH:40]=[CH:41][CH:42]=[CH:43][C:36]=2[NH:35][C:34]2[N:44]=[CH:45][CH:46]=[CH:47][C:33]1=2)[CH2:26][C:27]([O:29][CH3:30])=[O:28].C([O-])(=O)C.[NH4+]>C(O)(=O)C>[N:8]1[C:25]([CH2:26][C:27]([O:29][CH3:30])=[O:28])=[CH:31][N:32]2[C:38]=1[C:37]1[CH:40]=[CH:41][CH:42]=[CH:43][C:36]=1[NH:35][C:34]1[N:44]=[CH:45][CH:46]=[CH:47][C:33]2=1

Participants

5

Reactant 3

HCID 517165Ammonium AcetateHCID 67503655HCID 67503655, compoundHCID 86762110HCID 86762110, compound

Product 1

HCID 136390211HCID 136390211, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of 3-oxo-4-(6-oxo-6,11-dihydro-5H-benzo[e]pyrido[3,2-b][1,4]diazepin-5-yl)butanoate (crude product from step 1, 0.36 g, 1 eq.) in acetic acid (5 mL) was added ammonium acetate (0.385 g, 20 eq. based on the amount of starting material used in step 1). The reaction was stirred at 120° C. for 2 hours. The reaction was poured onto water (25 mL) and extracted with dichloromethane (2×25 mL). The combined extracts were washed with water (1×25 mL), saturated sodium bicarbonate (25 mL), brine (1×25 mL), dried over sodium sulfate, filtered and concentrated under reduced pressure. Purification by column chromatography (10% methanol in dichloromethane) gave the methyl 2-(9H-benzo[f]imidazo[1,2-d]pyrido[2,3-b][1,4]diazepin-2-yl)acetate (0.4 g). LCMS: 307 [M+H].

Workup

  1. additionThe reaction was poured onto water (25 mL)
  2. extractionextracted with dichloromethane (2×25 mL)
  3. washThe combined extracts were washed with water (1×25 mL), saturated sodium bicarbonate (25 mL), brine (1×25 mL)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customPurification by column chromatography (10% methanol in dichloromethane)

Sources & evidence

ORD record
ord-25870e97fd8341af91014c3fe2a1cbbc
Source dataset
uspto-grants-2013_10
Patent number
US08569331B2

Reaction notes

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