Formic Acid → HCID 89536255, compound

HRID 874683Notes

Reaction equation

HRID 874683 reaction equation
C(OC(=O)C)(=O)C.[CH:8]([OH:10])=O.[NH2:11][C:12]1[CH:31]=[CH:30][C:15]2[C:16]([N:19]3[C:27](=[O:28])[C:26]4[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=4)[C:20]3=[O:29])=[N:17][O:18][C:14]=2[CH:13]=1>C(Cl)Cl>[O:29]=[C:20]1[C:21]2[C:26](=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:27](=[O:28])[N:19]1[C:16]1[C:15]2[CH:30]=[CH:31][C:12]([NH:11][CH:8]=[O:10])=[CH:13][C:14]=2[O:18][N:17]=1

Participants

5

Reactant 3

HCID 284Formic AcidHCID 7918Acetic AnhydrideHCID 58290751HCID 58290751, compound

Product 1

HCID 89536255HCID 89536255, compoundYield 70.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
60 °C

Procedure

Acetic anhydride (2.63 mL, 27.9 mmol) was added to formic acid (1.04 mL, 27.9 mmol) at 0° C. The mixture was heated to 60° C. for 30 minutes. After that 2-(6-aminobenzo[d]isoxazol-3-yl)isoindoline-1,3-dione 1-4 (390 mg, 1.39 mmol) dissolved in CH2Cl2 (10 mL) was added at 0° C. The mixture was stirred for 1 h at room temperature. The mixture was concentrated and the residue was triturated with CH2Cl2/hexane (1:1) to give 300 mg (70%) of 1-5 as a pale yellow solid: 1H NMR (300 MHz, DMSO-d6) (rotamer ratio: s-cis/s-trans=3:1) δ 10.75 (0.75H, br s), 10.58 (0.25H, br d, J=11.3 Hz), 9.04 (0.25H, br d, J=11.3 Hz), 8.43 (0.75H, br s), 8.29 (0.75H, br s), 8.07 (2H, m), 7.99 (2H, m), 7.81 (1H, d, J=8.4 Hz), 7.80 (0.25H, br s), 7.43 (0.75H, d, J=8.4 Hz), 7.28 (0.25H, br d, J=8.4 Hz); ESI-MS m/z 308 [C16H9N3O4+H]+.

Workup

  1. additionwas added at 0° C
  2. concentrationThe mixture was concentrated
  3. customthe residue was triturated with CH2Cl2/hexane (1:1)

Sources & evidence

ORD record
ord-9394cc06a8ac4f0a9e95a91598d96ff1
Source dataset
uspto-grants-2015_03
Patent number
US08980916B2

Reaction notes

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