Hydrochloric Acid → 1-((3-methyl-1-(2-(1-methyl-1H-indol-5-ylamino)pyrimidin-4-yl)-1H-pyrazol-4-yl)methyl)azetidin-3-ol

HRID 539897Notes

Reaction equation

HRID 539897 reaction equation
[CH3:1][C:2]1[C:6](C=O)=[CH:5][N:4]([C:9]2[CH:14]=[CH:13][N:12]=[C:11]([NH:15][C:16]3[CH:17]=[C:18]4[C:22](=[CH:23][CH:24]=3)[N:21]([CH3:25])[CH:20]=[CH:19]4)[N:10]=2)[N:3]=1.Cl.[CH2:27]([N:29]([CH2:32][CH3:33])[CH2:30]C)C.[BH-](OC(C)=O)(OC(C)=O)[O:35]C(C)=O.[Na+]>ClCCl>[CH3:1][C:2]1[C:6]([CH2:30][N:29]2[CH2:27][CH:33]([OH:35])[CH2:32]2)=[CH:5][N:4]([C:9]2[CH:14]=[CH:13][N:12]=[C:11]([NH:15][C:16]3[CH:17]=[C:18]4[C:22](=[CH:23][CH:24]=3)[N:21]([CH3:25])[CH:20]=[CH:19]4)[N:10]=2)[N:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 866989873-methyl-1-(2-(1-methyl-1H-indol-5-ylamino)pyrimidin-4-yl)-1H-pyrazole-4-carbaldehyde

Product 1

HCID 716983751-((3-methyl-1-(2-(1-methyl-1H-indol-5-ylamino)pyrimidin-4-yl)-1H-pyrazol-4-yl)methyl)azetidin-3-ol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a slurry of intermediate 8 (77 mg, 0.23 mmol), 3-azetidinole hydrochloride (50 mg, 2 equiv.) and triethylamine (30 mL, 1 equiv.) in 20 mL of dichloromethane, was added NaBH(OAc)3 (146 mg, 3 equiv.) at room temperature. The reaction was stirred for 15 hour at room temperature and then quenched with 1N—NaOH. It was extracted with ethyl acetate and washed twice with brine. The collected organic layer was dried over anhydrous sodium sulfate and then concentrated in vacuo. The resulting residue was purified by recrystallization in a mixture of ethyl acetate and heptanes to afford desired Compound No. 140 as a pale yellow solid (62 mg, 69%); MS (ESI) m/z 390 [M+H]+.

Workup

  1. customquenched with 1N—NaOH
  2. extractionIt was extracted with ethyl acetate
  3. washwashed twice with brine
  4. dry with materialThe collected organic layer was dried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe resulting residue was purified by recrystallization in a mixture of ethyl acetate and heptanes

Sources & evidence

ORD record
ord-dd8714d6feb34dbc9e4ac1f73b890593
Source dataset
uspto-grants-2014_10
Patent number
US08871778B2

Reaction notes

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