Diethanolamine → HCID 59371676, compound

HRID 2095366Notes

Reaction equation

HRID 2095366 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:11][CH2:10][C@H:9]1[CH2:12][O:13][C:14]1[CH:15]=[C:16]([CH2:20][CH2:21][C:22]2[CH:23]=[C:24]([CH2:28][NH2:29])[CH:25]=[CH:26][CH:27]=2)[CH:17]=[N:18][CH:19]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[CH3:37][S:38](Cl)(=[O:40])=[O:39].N(CCO)CCO>C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:11][CH2:10][C@H:9]1[CH2:12][O:13][C:14]1[CH:15]=[C:16]([CH2:20][CH2:21][C:22]2[CH:23]=[C:24]([CH2:28][NH:29][S:38]([CH3:37])(=[O:40])=[O:39])[CH:25]=[CH:26][CH:27]=2)[CH:17]=[N:18][CH:19]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 8113DiethanolamineHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 59371316HCID 59371316, compound

Product 1

HCID 59371676HCID 59371676, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

3-[2-[5-[[1-(tert-Butoxycarbonyl)-(2S)-azetidinyl]methoxy]-3-pyridyl]ethyl]phenylmethylamine and triethylamine (1-2 equiv.) are dissolved in anhydrous CH2Cl2, and with exclusion of moisture and ice cooling a solution of methanesulfonyl chloride (1-1.5 equiv.) in CH2Cl2 is added dropwise. The mixture is stirred in the ice bath until no more starting amine is observed, then diethanolamine (0.2-0.7 equiv.) is added to quench the excess of methanesulfonyl chloride. The reaction mixture is evaporated and the residue chromatographed on silica gel with CH2Cl2/methanol. The product-containing fractions are evaporated, and the residue is dried in vacuo to obtain the sulfonamide.

Workup

  1. customto quench the excess of methanesulfonyl chloride
  2. customThe reaction mixture is evaporated
  3. customthe residue chromatographed on silica gel with CH2Cl2/methanol
  4. customThe product-containing fractions are evaporated
  5. customthe residue is dried in vacuo

Sources & evidence

ORD record
ord-a83c3cf1082c4368b878b65046be887d
Source dataset
uspto-grants-2013_05
Patent number
US08445684B2

Reaction notes

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