Methanol → HCID 58456304, compound

HRID 410566Notes

Reaction equation

HRID 410566 reaction equation
Cl[S:2]([N:5]=C=O)(=[O:4])=[O:3].CO.[CH3:10][O:11][C:12]1[CH:17]=[CH:16][N:15]=[C:14]([NH:18][C:19]2[CH:20]=[C:21]([C:26]3[S:30][C:29]([C:31]4(O)[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]4)=[N:28][CH:27]=3)[CH:22]=[C:23]([CH3:25])[CH:24]=2)[N:13]=1.C(N(CC)CC)C.[Cl:45]CCl>>[Cl:45][C:31]1([C:29]2[S:30][C:26]([C:21]3[CH:22]=[C:23]([CH3:25])[CH:24]=[C:19]([NH:18][C:14]4[N:13]=[C:12]([O:11][CH3:10])[CH:17]=[CH:16][N:15]=4)[CH:20]=3)=[CH:27][N:28]=2)[CH2:36][CH2:35][N:34]([S:2]([NH2:5])(=[O:4])=[O:3])[CH2:33][CH2:32]1

Participants

6

Reactant 5

HCID 887MethanolHCID 6344DichloromethaneHCID 8471TriethylamineHCID 70918Chlorosulfonyl isocyanateHCID 67248502HCID 67248502, compound

Product 1

HCID 58456304HCID 58456304, compound

Procedure

At 0° C., chlorosulfonyl isocyanate (16.38 μL, 0.189 mmol) in dichloromethane was added methanol (7.63 μL, 0.189 mmol). After stirring for 30 min, to the mixture was added 4-(5-{3-[(4-methoxypyrimidin-2-yl)amino]-5-methylphenyl}-1,3-thiazol-2-yl)piperidin-4-ol (50 mg, 0.126 mmol) and triethylamine (52.6 μL, 0.377 mmol). The reaction was aged for 20 min and ice bath removed, and stirred for 3 h. LCMS indicates product formation. The material was directly subject to column chromatography on silica gel (0-100% 10:1 ethyl acetate: methanol in hexanes) to afford:

Workup

  1. waitThe reaction was aged for 20 min
  2. customice bath removed
  3. stirringstirred for 3 h
  4. customto afford

Sources & evidence

ORD record
ord-f973023972fb4b01a2cc1932dbe6a02a
Source dataset
uspto-grants-2014_06
Patent number
US08759366B2

Reaction notes

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