Hydrazine → HCID 178505868, compound

HRID 222015Notes

Reaction equation

HRID 222015 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[C:11]3[C:18]4[CH2:19][CH2:20][C:21](=O)[C:22](=[CH:23][N:24](C)C)[C:17]=4[S:16][C:12]=3[N:13]=[CH:14][N:15]=2)[CH:5]=[CH:6][C:7]=1[F:8].[NH2:28]N>C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[N:15]=[CH:14][N:13]=[C:12]3[S:16][C:17]4[C:22]5[C:21]([CH2:20][CH2:19][C:18]=4[C:11]=23)=[N:28][NH:24][CH:23]=5)[CH:5]=[CH:6][C:7]=1[F:8]

Participants

4

Reactant 2

HCID 9321HydrazineHCID 67273682HCID 67273682, compound

Product 1

HCID 178505868HCID 178505868, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 4-(3-Chloro-4-fluoro-phenylamino)-8-dimethylaminomethylene-5,8-dihydro-6H-benzo[4,5]thieno[2,3-d]pyrimidin-7-one (100 mg, 0.25 mmol) in anhydrous ethanol (2 mL) was added hydrazine (12 mg, 0.37 mmol). The resulting mixture was stirred at rt for 5 h. The solid was filtered and washed with EtOAc and then with water. It yielded N-(3-chloro-4-fluorophenyl)-4,5-dihydro-2H-pyrimido[5′,4′:4,5]thieno[2,3-e]indazol-6-amine as a red solid (52 mg, 56%). 1H-NMR (DMSO-d6) δ 12.73 (s, 1H), 8.58 (s, 1H), 8.39 (s, 1H), 7.99 (s, 1H), 7.88 (s, 1H), 7.61 (m, 1H), 7.40 (t, 1H), 3.40 (t, 2H), 2.96 (t, 2H); LCMS RT=2.98 min; [M+H]+=372.3.

Workup

  1. filtrationThe solid was filtered
  2. washwashed with EtOAc

Sources & evidence

ORD record
ord-3b54492f2d3b4f0488228dc13373e660
Source dataset
uspto-grants-2012_06
Patent number
US08207172B2

Reaction notes

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