HCID 178486008, compound → HCID 178482191, compound

HRID 1922523Notes

Reaction equation

HRID 1922523 reaction equation
[CH3:1][N:2]([CH:10]1[CH2:15][CH2:14][CH:13]([N:16]2[C:25]3[C:20](=[CH:21][C:22]([NH:26][C:27]([C:29]4[S:30][CH:31]=[CH:32][CH:33]=4)=[NH:28])=[CH:23][CH:24]=3)[CH2:19][CH2:18][CH2:17]2)[CH2:12][CH2:11]1)C(=O)OC(C)(C)C.N1CCC(N2CCCCC3C=C(NC(C4SC=CC=4)=N)C=CC2=3)C1>CO.Cl>[CH3:1][NH:2][CH:10]1[CH2:11][CH2:12][CH:13]([N:16]2[C:25]3[C:20](=[CH:21][C:22]([NH:26][C:27]([C:29]4[S:30][CH:31]=[CH:32][CH:33]=4)=[NH:28])=[CH:23][CH:24]=3)[CH2:19][CH2:18][CH2:17]2)[CH2:14][CH2:15]1

Participants

5

Reactant 2

HCID 178486008HCID 178486008, compoundHCID 178511872HCID 178511872, compound

Product 1

HCID 178482191HCID 178482191, compoundYield 79%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Procedure

A solution of compound 11 (250 mg, 0.533 mmol) in methanol (10 mL) and 1M HCl (10 mL) was refluxed for 30 minutes and then concentrated. The residue was partitioned between 3N NaOH (50 mL) and CH2Cl2 (25 mL) and the product was extracted into CH2Cl2 (2×25 mL). The combined organic layers were dried (Na2SO4) and concentrated. This residue was subjected to flash chromatography on silica gel: 2% MeOH: 98% CH2Cl2 followed by 2.5% 2M ammonia in methanol; 97.5% CH2Cl2 to give a yellow-brown solid. (156 mg, 79% yield) 1H NMR (DMSO-d6) δ 7.66 (d, J=2.7 Hz, 1H), 7.54 (dd, J=0.9, 5.1 Hz, 1H), 7.06 (dd, J=3.6, 4.8 Hz, 1H), 6.63-6.41 (m, 3H), 6.21 (s, 2H), 3.55-3.46 (m, 1H), 3.35-3.30 (m, 1H) 3.13 (t, J=5.7 Hz, 2H), 2.63 (t, J=6.0 Hz, 2H), 2.26 (s, 3H), 2.10-1.75 (m, 6H), 1.60-1.45 (m, 2H), 1.39-1.32 (m, 2H). ESI-MS (m/z, %): 369 (MH+, 96), 338 (48), 258 (100), 185 (20), 148 (24), 140 (20); ESI-HRMS calculated for C21H29N4S (MH+): 369.2107, Observed: 369.2112; HPLC purity: 95.3%.

Workup

  1. concentrationconcentrated
  2. customThe residue was partitioned between 3N NaOH (50 mL) and CH2Cl2 (25 mL)
  3. extractionthe product was extracted into CH2Cl2 (2×25 mL)
  4. dry with materialThe combined organic layers were dried (Na2SO4)
  5. concentrationconcentrated
  6. custom97.5% CH2Cl2 to give a yellow-brown solid

Sources & evidence

ORD record
ord-56dded48e37d43dea40cff8b05bdd936
Source dataset
uspto-grants-2012_05
Patent number
US08173813B2

Reaction notes

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