Formic Acid → N-[4-(3,6-Dimethyl-4,10-dihydro-3H-2,3,4,9-tetraaza-benzo[f]azulene-9-carbonyl)-2-fluoro-benzyl]-formamide

HRID 220955Notes

Reaction equation

HRID 220955 reaction equation
[CH:1]([OH:3])=O.C(OC(=O)C)(=O)C.Cl.[NH2:12][CH2:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]([N:22]2[CH2:31][C:30]3[CH:29]=[N:28][N:27]([CH3:32])[C:26]=3[NH:25][C:24]3[CH:33]=[C:34]([CH3:37])[CH:35]=[CH:36][C:23]2=3)=[O:21])=[CH:16][C:15]=1[F:38].O>C(Cl)(Cl)Cl>[CH3:32][N:27]1[C:26]2[NH:25][C:24]3[CH:33]=[C:34]([CH3:37])[CH:35]=[CH:36][C:23]=3[N:22]([C:20]([C:17]3[CH:18]=[CH:19][C:14]([CH2:13][NH:12][CH:1]=[O:3])=[C:15]([F:38])[CH:16]=3)=[O:21])[CH2:31][C:30]=2[CH:29]=[N:28]1

Participants

6

Reactant 4

HCID 284Formic AcidHCID 962WaterHCID 7918Acetic AnhydrideHCID 135736009(4-Aminomethyl-3-fluoro-phenyl)-(3,6-dimethyl-4,10-dihydro-3H-2,3,4,9-tetraaza-benzo[f]azulen-9-yl)-methanone Hydrochloride

Product 1

HCID 136128434N-[4-(3,6-Dimethyl-4,10-dihydro-3H-2,3,4,9-tetraaza-benzo[f]azulene-9-carbonyl)-2-fluoro-benzyl]-formamideYield 40%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Formic acid (0.85 ml, 22.5 mmol) and acetic anhydride (1.4 ml, 13.5 mmol) were combined and stirred for 1 h at room temperature. (4-Aminomethyl-3-fluoro-phenyl)-(3,6-dimethyl-4,10-dihydro-3H-2,3,4,9-tetraaza-benzo[f]azulen-9-yl)-methanone hydrochloride from Example E98.2 (113 mg, 0.3 mmol) was added and the mixture was stirred for 1 h. Water (20 ml) was added and the mixture was stirred for 1 h. It was diluted with chloroform, washed with saturated NaHCO3 then brine, dried and concentrated in vacuo to yield a white solid identified as the title compound (48 mg, 40%).

Workup

  1. stirringthe mixture was stirred for 1 h
  2. stirringthe mixture was stirred for 1 h
  3. washwashed with saturated NaHCO3
  4. dry with materialbrine, dried
  5. concentrationconcentrated in vacuo
  6. customto yield a white solid

Sources & evidence

ORD record
ord-7a9c850b49bb41419f8a70dd41c82ce5
Source dataset
uspto-grants-2012_06
Patent number
US08202858B2

Reaction notes

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