Hydrochloric Acid → HCID 178524258, compound

HRID 1982940Notes

Reaction equation

HRID 1982940 reaction equation
C[O:2][C:3]([C:5]1[C:13]2[N:12]=[C:11]([C:14]3[C:22]4[C:17](=[N:18][CH:19]=[C:20]([C:23]5[C:32]6[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=6)[CH:26]=[N:25][CH:24]=5)[CH:21]=4)[NH:16][N:15]=3)[NH:10][C:9]=2[CH:8]=[CH:7][CH:6]=1)=[O:4].[OH-].[Na+].Cl>CO>[CH:26]1[C:27]2[C:32](=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:23]([C:20]2[CH:21]=[C:22]3[C:14]([C:11]4[NH:10][C:9]5[CH:8]=[CH:7][CH:6]=[C:5]([C:3]([OH:4])=[O:2])[C:13]=5[N:12]=4)=[N:15][NH:16][C:17]3=[N:18][CH:19]=2)=[CH:24][N:25]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 178497589HCID 178497589, compound

Product 1

HCID 178524258HCID 178524258, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

Compound 108 (1.5 g, 3.57 mmol) was suspended in a 10% aqueous sodium hydroxide solution (20 mL) and MeOH (10 mL). The suspension was heated to 80° C. for five hours. The reaction mixture was cooled to room temperature then acidified with 1M hydrochloric acid. The resulting precipitate was collected and the filtrate was concentrated to remove the residual MeOH. Additional precipitate was collected and combined with the previous portion and dried to afford Compound 17 (1.2 g, 83%) as a grey solid. 1H NMR (400 MHz, CD3OD) δ 9.81 (s, 1H), 9.14 (s, 1H), 8.89 (m, 2H), 8.61 (d, 1H, J=8.4 Hz), 8.23 (m, 2H), 8.06 (m, 2H), 8.03 (d, 1H, J=8.0 Hz), 7.44 (t, 1H, J=8.0 Hz); MS (ESI) m/z: 407 (M+H+).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customThe resulting precipitate was collected
  3. concentrationthe filtrate was concentrated
  4. customto remove the residual MeOH
  5. customAdditional precipitate was collected
  6. customdried

Sources & evidence

ORD record
ord-66812769a3e5457b9368e38e7bb82b4f
Source dataset
uspto-grants-2009_06
Patent number
US07541367B2

Reaction notes

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