Acetic acid--water (1/1) → HCID 16046968, compound

HRID 1690700Notes

Reaction equation

HRID 1690700 reaction equation
[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:12]=[CH:13][C:14]3[C:15]4[CH2:27][C:26]5[C:21](=[CH:22][CH:23]=[C:24]([NH2:28])[CH:25]=5)[C:16]=4[NH:17][C:18]=3[C:19]=2[F:20])=[CH:7][CH:6]=1)[CH2:2][CH2:3][CH3:4].CC(O)=O.O.[O:34]([C:36]#[N:37])[Na]>O.CCOC(C)=O>[CH2:1]([C:5]1[CH:6]=[CH:7][C:8]([C:11]2[CH:12]=[CH:13][C:14]3[C:15]4[CH2:27][C:26]5[C:21](=[CH:22][CH:23]=[C:24]([NH:28][C:36]([NH2:37])=[O:34])[CH:25]=5)[C:16]=4[NH:17][C:18]=3[C:19]=2[F:20])=[CH:9][CH:10]=1)[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 3

HCID 21899381Acetic acid--water (1/1)HCID 576185157-(4-Butylphenyl)-6-fluoro-5,10-dihydroindeno[1,2-b]indol-2-amineHCID 178418852HCID 178418852, compound2×

Product 1

HCID 16046968HCID 16046968, compoundYield 36%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
25 °C

Procedure

To a suspension of 7-(4-Butyl-phenyl)-6-fluoro-5,10-dihydro-indeno[1,2-b]indol-2-ylamine (25 mg, 0.068 mmol, 1 eq.) in a 1:1 v/v mixture of AcOH/H2O (1 mL) is added a solution of NaOCN (4.4 mg, 0.068 mmol, 1 eq.) in H2O (1 mL). The resulting mixture is stirred at 25° C. for 2 h, at which point an additional NaOCN (4.4 mg, 0.068 mmol, 1 eq.) is added to the reaction. The resulting mixture is stirred at 25° C. for an additional 12 h. The reaction is diluted with EtOAc and sequentially washed with H2O, saturated aqueous NaHCO3, and saturated aqueous NaCl. The resulting organic solution is dried over Na2SO4. After concentration, the crude product is purified by preparative RP LC-MS to give [7-(4-Butyl-phenyl)-6-fluoro-5,10-dihydro-indeno[1,2-b]indol-2-yl]-urea (10 mg, 36% yield): 1H NMR (Acetone-d6) δ 11.09 (s, 1H), 8.26 (s, 1H), 7.89 (s, 1H), 7.59 (d, 2H), 7.58 (s, 1H), 7.48 (d, 1H), 7.42 (d, 1H), 7.33 (d, 2H), 7.18 (dd, 1H), 5.53 (bs), 3.72 (s, 2H), 2.72 (t, 2H), 1.72-1.64 (m, 2H), 1.49-1.36 (m, 2H), 0.96 (t, 3H); LC/MS calculated for [M+H]+ C26H24FN3O: 414.2, found: 414.2.

Workup

  1. additionis added to the reaction
  2. washsequentially washed with H2O, saturated aqueous NaHCO3, and saturated aqueous NaCl
  3. dry with materialThe resulting organic solution is dried over Na2SO4
  4. concentrationAfter concentration
  5. customthe crude product is purified by preparative RP LC-MS

Sources & evidence

ORD record
ord-fd01dcc9f15c4006b45b8acee19b2f68
Source dataset
uspto-grants-2012_04
Patent number
US08153671B2

Reaction notes

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