HCID 178480390, compound → HCID 178482191, compound

HRID 1922524Notes

Reaction equation

HRID 1922524 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.CN1CCC(N2C3C(=CC(NC(C4SC=CC=4)=N)=CC=3)CC2)C1.O1CCN(CCN2C3C(=CC(NC(C4SC=CC=4)=N)=CC=3)CCC2)CC1.CN1CCC(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

7

Reactant 4

HCID 178480390HCID 178480390, compoundHCID 178480393HCID 178480393, compoundHCID 178486008HCID 178486008, compoundHCID 178511877HCID 178511877, compound

Product 1

HCID 178482191HCID 178482191, compoundYield 55%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Procedure

A solution of compound 5 (250 mg, 0.533 mmol) in MeOH (10 mL) and 1M HCl (10 mL) was refluxed for half an hour 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% methanol: 98% CH2Cl2 followed by 2.5% 2M ammonia in methanol; 97.5% CH2Cl2 to give a yellow-brown solid. (108 mg, 55% yield) 1H NMR (DMSO-d6) δ 7.67 (d, J=3.0 Hz, 1H), 7.54 (d, J=5.1 Hz, 1H), 7.07 (dd, J=3.9, 5.1 Hz), 6.62-6.47 (m, 3H), 6.21 (s, 2H), 3.57-3.50 (m, 1H), 3.11 (t, J=5.4 Hz, 2H), 2.63 (t, J=6.3 Hz, 2H), 2.28 (s, 3H), 2.24-2.20 (m, 1H), 1.98-1.92 (m, 2H), 1.82-1.77 (m, 2H), 1.70-1.65 (m, 2H), 1.59-1.47 (m, 2H), 1.24-1.11 (m, 2H). ESI-MS (m/z, %): 369 (MH+, 82), 338 (100), 258 (21), 185 (50), 148 (64), 140 (46); ESI-HRMS calculated for C21H29N4S (MH+): 369.2107, Observed: 369.2104; 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-789ef62e14ae49419e43909f8956af9e
Source dataset
uspto-grants-2012_05
Patent number
US08173813B2

Reaction notes

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