Triethylamine → HCID 11475935, compound

HRID 1178769Notes

Reaction equation

HRID 1178769 reaction equation
C(OC(=O)[N:7]([CH2:23][CH2:24][NH:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[NH:32][S:33]([CH3:36])(=[O:35])=[O:34])[CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([N:17]2[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]2)=[O:16])[CH:10]=1)(C)(C)C.C(OC(=O)N(CCNC1C=CC=CC=1N)CC1C=CC=C(C(N2CCCCC2)=O)C=1)(C)(C)C.CCN(CC)CC.CS(Cl)(=O)=O.[NH4+].[Cl-]>C(Cl)Cl.O>[N:17]1([C:15]([C:11]2[CH:10]=[C:9]([CH:14]=[CH:13][CH:12]=2)[CH2:8][NH:7][CH2:23][CH2:24][NH:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=2[NH:32][S:33]([CH3:36])(=[O:35])=[O:34])=[O:16])[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 31297Methanesulfonyl chlorideHCID 67045852HCID 67045852, compoundHCID 67046058HCID 67046058, compound

Product 1

HCID 11475935HCID 11475935, compoundYield 51%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
25 °C

Procedure

[2-(2-Methanesulfonylamino-phenylamino)-ethyl]-[3-(piperidine-1-carbonyl)-benzyl]-carbamic acid tert-butyl ester. To a solution of [2-(2-amino-phenylamino)-ethyl]-[3-(piperidine-1-carbonyl)-benzyl]-carbamic acid tert-butyl ester (Example 13, step B; 0.10 g, 0.22 mmol) in CH2Cl2 (4 mL) was added Et3N (0.033 g, 0.33 mmol) and methanesulfonyl chloride (0.028 g, 0.24 mmol), and the resulting mixture was stirred at 25° C. for 17 h. The reaction mixture was treated with satd NH4Cl (10 mL), H2O (10 mL) and CH2Cl2 (20 mL), and the aqueous layer was extracted with CH2Cl2 (3×20 mL). The combined organic layers were washed with brine, dried (MgSO4), filtered, and concentrated under reduced pressure. The crude residue was purified by preparative TLC (30% acetone/hexanes) to provide the desired product (0.060 g, 51%). MS (ESI): mass calculated for C27H38N4O5S, 530.26. m/z found, 531.2 [M+H]+.

Workup

  1. extractionthe aqueous layer was extracted with CH2Cl2 (3×20 mL)
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe crude residue was purified by preparative TLC (30% acetone/hexanes)

Sources & evidence

ORD record
ord-f252184b2fa549c5a1d4503b1ef4e57e
Source dataset
uspto-grants-2007_10
Patent number
US07276610B2

Reaction notes

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