Ethanol → 4-(6,7-Dihydropyrido[3,2-b]thieno[2,3-d]oxepin-9-yl)-(5-(2-chlorophenyl))-thiazol-2-amine

HRID 1949736Notes

Reaction equation

HRID 1949736 reaction equation
[N:1]1[C:11]2[C:10]3[S:12][C:13]([CH:15](Br)[C:16]([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=4[Cl:24])=O)=[CH:14][C:9]=3[CH2:8][CH2:7][O:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.[NH2:26][C:27]([NH2:29])=[S:28].C(O)C>>[N:1]1[C:11]2[C:10]3[S:12][C:13]([C:15]4[N:26]=[C:27]([NH2:29])[S:28][C:16]=4[C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=4[Cl:24])=[CH:14][C:9]=3[CH2:8][CH2:7][O:6][C:5]=2[CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 2723790ThioureaHCID 866348406,7-Dihydropyrido[3,2-b]thieno[2,3-d]oxepin-9-yl-(2-chlorophenyl)-2-bromoethanone

Product 1

HCID 442425624-(6,7-Dihydropyrido[3,2-b]thieno[2,3-d]oxepin-9-yl)-(5-(2-chlorophenyl))-thiazol-2-amine

Procedure

6,7-Dihydropyrido[3,2-b]thieno[2,3-d]oxepin-9-yl-(2-chlorophenyl)-2-bromoethanone from Example 37 (100.0 mg, 0.230 mmol) and thiourea (20.14 mg, 0.264 mmol) were heated in ethanol (5 mL, 80 mmol) for 1 hour. The solvent was evaporated to half of the volume, whereupon the product crystallized upon standing. The product 165 was collected by filtration and washed with cold ethanol (yield 43 mg, 45%). 1H NMR (400 MHz, DMSO) δ 8.15 (d, J=3.2, 1H), 7.66 (d, J=8.2, 1H), 7.54 (t, J=7.6, 2H), 7.47 (t, J=7.4, 1H), 7.36 (d, J=8.1, 1H), 7.16 (dd, J=4.5, 8.1, 1H), 6.73 (s, 1H), 5.80-4.90 (m, 2H), 4.24 (t, J=4.7, 2H), 3.04 (t, J=4.7, 2H). MS (ESI+) 412.1

Workup

  1. customThe solvent was evaporated to half of the volume, whereupon the product
  2. customcrystallized
  3. filtrationThe product 165 was collected by filtration
  4. washwashed with cold ethanol (yield 43 mg, 45%)

Sources & evidence

ORD record
ord-0646f13ede0c4e56a589c5a84d1a5b15
Source dataset
uspto-grants-2013_03
Patent number
US08399690B2

Reaction notes

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