HCID 53416493, compound → HCID 67229897, compound

HRID 600810

Reaction equation

HRID 600810 reaction equation
[C:1]([O:5][C:6](=[O:21])[NH:7][CH:8]1[CH2:17][CH2:16][C:15]2[C:10](=[C:11]([N:18]=[C:19]=S)[CH:12]=[CH:13][CH:14]=2)[CH2:9]1)([CH3:4])([CH3:3])[CH3:2].C(OC1CC2C(CC=1)=CC=CC=2N=C=S)C.[N:38]([CH2:41][C:42]([C:44]1[CH:49]=[CH:48][C:47]([C:50]([F:53])([F:52])[F:51])=[CH:46][CH:45]=1)=[O:43])=[N+]=[N-]>>[C:1]([O:5][C:6](=[O:21])[NH:7][CH:8]1[CH2:17][CH2:16][C:15]2[C:10](=[C:11]([NH:18][C:19]3[O:43][C:42]([C:44]4[CH:49]=[CH:48][C:47]([C:50]([F:51])([F:52])[F:53])=[CH:46][CH:45]=4)=[CH:41][N:38]=3)[CH:12]=[CH:13][CH:14]=2)[CH2:9]1)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 3

HCID 53416493HCID 53416493, compoundHCID 866096122-Ethoxy-8-isothiocyanato-1,4-dihydronaphthaleneHCID 86609614HCID 86609614, compound

Product 1

HCID 67229897HCID 67229897, compoundYield 37%

Procedure

The title compound was prepared using the procedure as described in Example 1H, substituting the product of Example 20F (215 mg, 0.706 mmol) for the product of Example 1F, and the product of Example 1G (194 mg, 0.848 mmol). The crude product was purified by flash chromatography eluting with 20% EtOAc/hexane which gave 123 mg (37%) of the title compound as a white solid. 1H NMR (DMSO-d6) δ 9.32 (br s, 1H), 7.75 (m, 4H), 7.60 (s, 1H), 7.55 (d, J=7.8 Hz, 1H), 7.12 (t, J=7.8 Hz, 1H), 6.98 (br d, 1H), 6.88 (d, J=7.5 Hz, 1H), 3.64 (m, 1H), 3.02 (m, 1H), 2.84 (m, 2H), 2.42 (m, 1H), 1.87 (m, 1H), 1.60 (m, 1H), 1.39 (s, 9H); MS (ESI+) m/z 474 (M+H)+.

Workup

  1. customThe title compound was prepared
  2. customThe crude product was purified by flash chromatography
  3. washeluting with 20% EtOAc/hexane which

Sources & evidence

ORD record
ord-b265e1e72171414a8146525a81942c31
Source dataset
uspto-grants-2011_03
Patent number
US07902236B2

Linked notes

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