Ammonia → HCID 86669687, compound

HRID 1623948Notes

Reaction equation

HRID 1623948 reaction equation
C(O[C:4]([C:6]1([NH:10][C:11]([C:13]2[C:14]3[CH2:15][C@@H:16]4[CH2:29][C@@H:17]4[C:18]=3[N:19]([C:21]3[CH:26]=[CH:25][C:24]([F:27])=[CH:23][C:22]=3[F:28])[N:20]=2)=[O:12])[CH2:9][CH2:8][CH2:7]1)=[O:5])C.[NH3:30]>CO>[C:4]([C:6]1([NH:10][C:11]([CH:13]2[NH:20][N:19]([C:21]3[CH:26]=[CH:25][C:24]([F:27])=[CH:23][C:22]=3[F:28])[C:18]3[C@H:17]4[CH2:29][C@H:16]4[CH2:15][C:14]2=3)=[O:12])[CH2:7][CH2:8][CH2:9]1)(=[O:5])[NH2:30]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 68182445HCID 68182445, compound

Product 1

HCID 86669687HCID 86669687, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
65 °C

Procedure

1-{[(1aS,5aS)-2-(2,4-Difluoro-phenyl)-1a,2,5,5a-tetrahydro-1H-2,3-diaza-cyclopropa[a]pentalene-4-carbonyl]-amino}-cyclobutanecarboxylic acid ethyl ester (20 mg, 0.05 mmol) was dissolved in 7 N ammonia in methanol (4 mL). The sealed reaction vial was stirred at 65° C. for 48 h. The solvent was evaporated, and the residue was purified by preparative TLC plate to give the title compound (14 mg) as a white solid. LCMS m/z=373.3 [M+H]+; 1H NMR (400 MHz, DMSO-d6) δ ppm 0.46 (td, J=4.6 and 3.5 Hz, 1H), 1.16-1.20 (m, 1H), 1.82-1.94 (m, 1H), 2.18-2.31 (m, 4H), 2.50 (m, buried, 3H), 2.80 (d, J=16.3 Hz, 1H), 2.92 (dd, J=16.3 and 6.3 Hz, 1H), 6.85 (s, 1H), 6.96 (s, 1H), 7.32-7.38 (m, 1H), 7.61-7.68 (m, 1H), 7.81-7.88 (m, 1H), 8.28 (s, 1H).

Workup

  1. customThe sealed reaction vial
  2. customThe solvent was evaporated
  3. customthe residue was purified by preparative TLC plate

Sources & evidence

ORD record
ord-9d383668044b44f881135f53c2df4987
Source dataset
uspto-grants-2014_07
Patent number
US08778950B2

Reaction notes

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