Acetic Anhydride → HCID 22291714, compound

HRID 968136Notes

Reaction equation

HRID 968136 reaction equation
[NH2:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([N:11]2[C:19]3[C:18]4[CH:20]=[C:21]([NH:24][C:25](=[O:33])[C:26]5[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=5[Cl:32])[CH:22]=[CH:23][C:17]=4[CH2:16][CH2:15][C:14]=3[C:13]([C:34]([NH2:36])=[O:35])=[N:12]2)=[CH:7][CH:6]=1)(=[O:4])=[O:3].C(N(CC)CC)C.[C:44](OC(=O)C)(=[O:46])[CH3:45]>C1COCC1.CN(C1C=CN=CC=1)C>[C:44]([NH:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([N:11]2[C:19]3[C:18]4[CH:20]=[C:21]([NH:24][C:25](=[O:33])[C:26]5[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=5[Cl:32])[CH:22]=[CH:23][C:17]=4[CH2:16][CH2:15][C:14]=3[C:13]([C:34]([NH2:36])=[O:35])=[N:12]2)=[CH:7][CH:6]=1)(=[O:4])=[O:3])(=[O:46])[CH3:45]

Participants

6

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 22291809HCID 22291809, compound

Product 1

HCID 22291714HCID 22291714, compoundYield 70.2%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a stirring solution of 1-[4-(aminosulfonyl)phenyl]-8-[(2-chlorobenzoyl)amino]-4,5-dihydro-1H-benzo[g]indazole-3-carboxamide (2967 mg, 5.7 mmol) in THF (120 mL) was added DMAP (348 mg, 2.8 mmol), then tri-ethyl amine (0.95 mL, 6.8 mmol), followed by acetic anhydride (1.62 mL, 17.1 mmol). The reaction mixture was stirred at room temperature for overnight and then concentrated. To the residue was added 5% aq. NaHCO3 (100 mL). All compounds were dissolved. The aq. Layer was washed with EA (100 mL×2), CH2Cl2 (100 mL). The aq. layer was separated. To the aq. Layer was added 1N HCl to pH=6. A white precipitate was formed. It was filtered and washed with ether to give a white solid. The solid was dried under reduced pressure at 45° C. to give 1-{4-[(acetylamino)sulfonyl]phenyl}-8-[(2-chlorobenzoyl)amino]-4,5-dihydro-1H-benzo[g]indazole-3-carboxamide (2255.4 mg, 70%).

Workup

  1. concentrationconcentrated
  2. additionTo the residue was added 5% aq. NaHCO3 (100 mL)
  3. dissolutionAll compounds were dissolved
  4. washThe aq. Layer was washed with EA (100 mL×2), CH2Cl2 (100 mL)
  5. customThe aq. layer was separated
  6. additionTo the aq. Layer was added 1N HCl to pH=6
  7. customA white precipitate was formed
  8. filtrationIt was filtered
  9. washwashed with ether
  10. customto give a white solid
  11. customThe solid was dried under reduced pressure at 45° C.

Sources & evidence

ORD record
ord-97143aa525bd4c89bccae0937ae1318c
Source dataset
uspto-grants-2005_10
Patent number
US06956052B2

Reaction notes

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