Triethylamine → HCID 66892955, compound

HRID 448594Notes

Reaction equation

HRID 448594 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:11][CH:10]([OH:12])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[N+](C1C=CC([C:27](Cl)=[O:28])=CC=1)([O-])=O.[CH3:32][S:33]([C:36]1[CH:37]=[C:38]2[C:42](=[CH:43][CH:44]=1)[N:41]([C:45]1[CH:50]=[C:49]([O:51][CH:52]3[CH2:57][CH2:56][NH:55][CH2:54][CH2:53]3)[N:48]=[CH:47][N:46]=1)[CH2:40][CH2:39]2)(=[O:35])=[O:34]>C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:11][CH:10]([O:12][C:27]([N:55]2[CH2:56][CH2:57][CH:52]([O:51][C:49]3[CH:50]=[C:45]([N:41]4[C:42]5[C:38](=[CH:37][C:36]([S:33]([CH3:32])(=[O:35])=[O:34])=[CH:44][CH:43]=5)[CH2:39][CH2:40]4)[N:46]=[CH:47][N:48]=3)[CH2:53][CH2:54]2)=[O:28])[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 85024-Nitrobenzoyl chlorideHCID 2756801Tert-butyl 3-hydroxyazetidine-1-carboxylateHCID 667096685-(Methylsulfonyl)-1-(6-(piperidin-4-yloxy)pyrimidin-4-yl)indoline

Product 1

HCID 66892955HCID 66892955, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

3-Hydroxy-azetidine-1-carboxylic acid tert-butyl ester (0.17 g, 1 mmol) was dissolved in 3 mL of DCM with triethylamine (0.28 mL, 2 mmol). 4-Nitro-benzoyl chloride (0.2 g, 1 mmol) was added and the mixture was stirred at room temperature for 12 h. A fifth of the solution was reacted with 4b (75 mg, 0.2 mmol). The mixture was stirred at room temperature for 8 h, diluted with DCM and washed with saturated NaHCO3. The organic layer was evaporated to afford crude 22a, LCMS 574.2 (MH+).

Workup

  1. stirringThe mixture was stirred at room temperature for 8 h
  2. washwashed with saturated NaHCO3
  3. customThe organic layer was evaporated

Sources & evidence

ORD record
ord-1c74066d8f7740f69c5c780c4855940b
Source dataset
uspto-grants-2013_07
Patent number
US08481731B2

Reaction notes

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