Water → HCID 178516769, compound

HRID 1506179Notes

Reaction equation

HRID 1506179 reaction equation
[C:1]1([C@@H:13]2[CH2:18][CH2:17][C@H:16]([CH:19]=O)[CH2:15][CH2:14]2)[N:2]=[N:3][N:4]2[C:9]=1[C:8]1[CH:10]=[CH:11][NH:12][C:7]=1[N:6]=[CH:5]2.Cl.[OH:22][CH:23]1[CH2:26][NH:25][CH2:24]1.B.N1C=CC=CC=1C.O>CO.O1CCCC1.C(O)(=O)C>[C:1]1([C@@H:13]2[CH2:18][CH2:17][C@H:16]([CH2:19][N:25]3[CH2:26][CH:23]([OH:22])[CH2:24]3)[CH2:15][CH2:14]2)[N:2]=[N:3][N:4]2[C:9]=1[C:8]1[CH:10]=[CH:11][NH:12][C:7]=1[N:6]=[CH:5]2

Participants

8

Reactant 4

HCID 962WaterHCID 27592903-Hydroxyazetidine hydrochlorideHCID 16217944Borane;2-methylpyridineHCID 178520934HCID 178520934, compound

Product 1

HCID 178516769HCID 178516769, compoundYield 31%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

cis-4-(7H-Pyrrolo[3,2-e][1,2,3]triazolo[1,5-c]pyrimidin-1-yl)cyclohexanecarbaldehyde (30.0 mg, 0.111 mmol) in methanol (2 mL), tetrahydrofuran (1 mL) and acetic acid (100 μL) was mixed with 3-hydroxyazetidine hydrochloride (41.3 mg, 0.334 mmol) and stirred at room temperature for 1 hour. The reaction mixture was mixed with 2-picoline borane (23.8 mg, 0.334 mmol) and stirred at room temperature for 14 hours. After addition of water, the reaction mixture was extracted with ethyl acetate. The aqueous layer was adjusted to pH 10 with 1 M aqueous sodium hydroxide, and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was washed with hexane/ethyl acetate (5/1 (v/v)) to give the title compound as a colorless solid (7.40 mg, yield 31%).

Workup

  1. stirringstirred at room temperature for 14 hours
  2. extractionthe reaction mixture was extracted with ethyl acetate
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. washThe residue was washed with hexane/ethyl acetate (5/1 (v/v))

Sources & evidence

ORD record
ord-124355eee90d4f86b3c86b79c204e6d6
Source dataset
uspto-grants-2015_12
Patent number
US09216999B2

Reaction notes

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