Ethanol → 4-[4-(3-Fluoro-benzyloxy)-2-(1,4,9,9b-tetraaza-cyclopenta[a]naphthalen-6-ylamino)-phenylsulfanyl]-phenol

HRID 883835Notes

Reaction equation

HRID 883835 reaction equation
Cl[C:2]1[N:11]=[CH:10][N:9]=[C:8]2[C:3]=1[CH:4]=[N:5][C:6]1[N:7]2[N:12]=[CH:13][CH:14]=1.NC1[CH:21]=[C:20]([O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([F:30])[CH:25]=2)[CH:19]=[CH:18][C:17]=1[S:31][C:32]1[CH:37]=[CH:36][C:35]([OH:38])=[CH:34][CH:33]=1.[CH2:39](O)[CH3:40]>>[F:30][C:26]1[CH:25]=[C:24]([CH:29]=[CH:28][CH:27]=1)[CH2:23][O:22][C:20]1[CH:19]=[CH:18][C:17]([S:31][C:32]2[CH:33]=[CH:34][C:35]([OH:38])=[CH:36][CH:37]=2)=[C:10]([NH:11][C:2]2[CH:40]=[CH:39][N:9]=[C:8]3[C:3]=2[CH:4]=[N:5][C:6]2[N:7]3[N:12]=[CH:13][CH:14]=2)[CH:21]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 668086774-[2-Amino-4-(3-fluoro-benzyloxy)-phenylsulfanyl]-phenolHCID 866548856-Chloro-1,4,7,9,9b-pentaaza-cyclopenta[a]naphthalene

Product 1

HCID 672517734-[4-(3-Fluoro-benzyloxy)-2-(1,4,9,9b-tetraaza-cyclopenta[a]naphthalen-6-ylamino)-phenylsulfanyl]-phenolYield 8.5%

Procedure

The product from Example 1b (82 mg, 0.40 mmol) was reacted with 4-[2-Amino-4-(3-fluoro-benzyloxy)-phenylsulfanyl]-phenol (148 mg, 0.40 mmol) in 5 mL of ethanol at 70° C. for 24 hours. After cooling to room temperature the solvent was removed under vacuum and the product was purified by HPLC with ammonium acetate to give the title compound as a pale yellow solid (18 mg, 8.5%). 1H NMR (DMSO-d6) δ ppm: 5.15 (brs, 2H) 6.60 (d, J=8.86 Hz, 2H), 6.95 (d, J=2.75 Hz, 1H), 7.01 (dd, J=2.96 Hz, 2.75 Hz, 1H), 7.12 (d, J=8.46 Hz, 2 h), 7.16-7.20 (m, 3H), 7.30 (m, 2H), 8.31 (d, J=2.32 Hz, 1H), 8.63 (brs, 1H), 9.40 (s, 1H) 10.51 (br s, 1H); (ESI+) m/z 511 (M+H)+.

Workup

  1. customwas removed under vacuum
  2. customthe product was purified by HPLC with ammonium acetate

Sources & evidence

ORD record
ord-04318ed322804481bde231606babf9bb
Source dataset
uspto-grants-2012_08
Patent number
US08236950B2

Reaction notes

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