Hydrochloric Acid → N-(4-(1H-Pyrrolo[3,2-b]pyridin-7-yloxy)-3-fluorophenylcarbamothioyl)-2-(2,6-dichlorophenyl)acetamide dihydrochloride

HRID 1261339Notes

Reaction equation

HRID 1261339 reaction equation
[NH:1]1[C:9]2[C:4](=[N:5][CH:6]=[CH:7][C:8]=2[O:10][C:11]2[CH:16]=[CH:15][C:14]([NH2:17])=[CH:13][C:12]=2[F:18])[CH:3]=[CH:2]1.N1C2C(=NC=CC=2OC2C=CC(NC(NC(=O)CC3C=CC=CC=3)=S)=CC=2F)C=C1.[N-]=C=S.[Cl:52][C:53]1[CH:58]=[CH:57][CH:56]=[C:55]([Cl:59])[C:54]=1[CH2:60][C:61]([N:63]=[C:64]=[S:65])=[O:62].[ClH:66]>CO>[ClH:52].[ClH:66].[NH:1]1[C:9]2[C:4](=[N:5][CH:6]=[CH:7][C:8]=2[O:10][C:11]2[CH:16]=[CH:15][C:14]([NH:17][C:64]([NH:63][C:61](=[O:62])[CH2:60][C:54]3[C:53]([Cl:52])=[CH:58][CH:57]=[CH:56][C:55]=3[Cl:59])=[S:65])=[CH:13][C:12]=2[F:18])[CH:3]=[CH:2]1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 594244392-(2,6-Dichlorophenyl)acetyl isothiocyanateHCID 59424591N-(4-(1H-Pyrrolo[3,2-b]pyridin-7-yloxy)-3-fluorophenylcarbamothioyl)-2-phenyl acetamideHCID 594245934-(1H-Pyrrolo[3,2-b]pyridin-7-yloxy)-3-fluorobenzenamineHCID 178418790HCID 178418790, compound

Product 1

HCID 86604194N-(4-(1H-Pyrrolo[3,2-b]pyridin-7-yloxy)-3-fluorophenylcarbamothioyl)-2-(2,6-dichlorophenyl)acetamide dihydrochlorideYield 48%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Starting from the compound 268 and following the procedure described above for the synthesis of compound 269a (example 221) but replacing 2-phenylacethyl isothiocyanate with 2-(2,6-dichlorophenyl)acetyl isothiocyanate, a white solid was obtained. This material was dissolved in MeOH and treated with HCl (1 mL, 1.0M in ether). Solvents were removed under the reduced pressure and the residue was lyophilized, to afford the title compound 269b (48% yield) as a yellowish solid. 1H NMR (DMSO-d6) δ (ppm): 13.29(s, 1H), 12.32(s, 1H), 12.05(s, 1H), 8.52(d, 1H,), 8.14(m, 2H), 7.64(m, 2H), 7.51(d, 1H), 7.37(dd, 1H), 6.86(m, 1H), 6.81(dd, 1H), 4.22(s, 2H), MS (m/z): 489.1(M+H) (found).

Workup

  1. customa white solid was obtained
  2. customSolvents were removed under the reduced pressure

Sources & evidence

ORD record
ord-1417c06bd2c140338609d9ae324eba52
Source dataset
uspto-grants-2013_06
Patent number
US08470850B2

Reaction notes

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