Triethylamine → HCID 90412762, compound

HRID 1521986Notes

Reaction equation

HRID 1521986 reaction equation
[CH:1]12[NH:8][CH:5]([CH2:6][CH2:7]1)[CH2:4][C:3]([C:9]1[NH:26][C:12]3=[N:13][CH:14]=[CH:15][C:16]([C:17]4[CH:22]=[C:21]([F:23])[CH:20]=[CH:19][C:18]=4[O:24][CH3:25])=[C:11]3[CH:10]=1)=[CH:2]2.[CH3:27][S:28](Cl)(=[O:30])=[O:29].C(N(CC)CC)C.C(=O)(O)[O-].[Na+]>CN(C)C=O.[Cl-].[Na+].O>[F:23][C:21]1[CH:20]=[CH:19][C:18]([O:24][CH3:25])=[C:17]([C:16]2[CH:15]=[CH:14][N:13]=[C:12]3[NH:26][C:9]([C:3]4[CH2:4][CH:5]5[N:8]([S:28]([CH3:27])(=[O:30])=[O:29])[CH:1]([CH2:7][CH2:6]5)[CH:2]=4)=[CH:10][C:11]=23)[CH:22]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 90414170HCID 90414170, compound

Product 1

HCID 90412762HCID 90412762, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of Example 223C (80.0 mg, 0.189 mmol) in N,N-dimethylformamide (2 mL) was added methanesulfonyl chloride (0.030 mL, 0.379 mmol) and triethylamine (0.158 mL, 1.137 mmol) and the mixture was stirred for 3 hours. The mixture was treated with brine and aqueous sodium bicarbonate and extracted with ethyl acetate (twice). The combined organic layers were dried over magnesium sulfate, filtered, concentrated, and purified on silica gel using an ISCO Companion eluting with heptanes/ethyl acetate (1:9 to 0:10) to give the title compound. 1H NMR (400 MHz, DMSO-d6) δ 1.63-1.74 (m, 1H), 1.91-2.14 (m, 2H), 2.15-2.27 (m, 1H), 2.92-3.00 (m, 4H), 3.74 (s, 3H), 4.32-4.40 (m, 1H), 4.44 (t, J=5.8 Hz, 1H), 6.22 (s, 1H), 6.79 (d, J=6.0 Hz, 1H), 7.03 (d, J=4.9 Hz, 1H), 7.15-7.31 (m, 3H), 8.20 (d, J=4.9 Hz, 1H), 11.73-11.86 (m, 1H). MS (ESI+) m/z 428.1 (M+H)+.

Workup

  1. extractionextracted with ethyl acetate (twice)
  2. dry with materialThe combined organic layers were dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. custompurified on silica gel using an ISCO Companion
  6. washeluting with heptanes/ethyl acetate (1:9 to 0:10)

Sources & evidence

ORD record
ord-5d08dc0f337141cc835d7590655830e3
Source dataset
uspto-grants-2015_07
Patent number
US09073922B2

Reaction notes

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