Aluminium lithium hydride → HCID 86732439, compound

HRID 1776410Notes

Reaction equation

HRID 1776410 reaction equation
[Cl:1][C:2]1[C:11]([CH2:12][N:13]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:15]([C:22]3[N:27]=[C:26]([NH:28][C:29]4[CH:34]=[CH:33][N:32]=[CH:31][CH:30]=4)[C:25]([O:35][CH3:36])=[CH:24][N:23]=3)=[N:14]2)=[C:10]([Cl:37])[CH:9]=[CH:8][C:3]=1[C:4](OC)=[O:5].[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[Cl:1][C:2]1[C:11]([CH2:12][N:13]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:15]([C:22]3[N:27]=[C:26]([NH:28][C:29]4[CH:34]=[CH:33][N:32]=[CH:31][CH:30]=4)[C:25]([O:35][CH3:36])=[CH:24][N:23]=3)=[N:14]2)=[C:10]([Cl:37])[CH:9]=[CH:8][C:3]=1[CH2:4][OH:5]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 71553532HCID 71553532, compound

Product 1

HCID 86732439HCID 86732439, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

80 mg of methyl 2,4-dichloro-3-({3-[5-methoxy-4-(pyridin-4-ylamino)pyrimidin-2-yl]-1H-indazol-1-yl}methyl)benzoate (2-16-1, 0.149 mmol, 1. eq.) was suspended in 2.4 ml of dry tetrahydrofuran under nitrogen atmosphere. The suspension was cooled with an ice bath to +3° C., upon which 254 μl of a 1 M lithium aluminium hydride solution in tetrahydrofuran (0.254 mmol, 1.7 eq.) were added dropwise. The ice bath was remove and the mixture was stirred at room temperature for 30 minutes. Then the mixture was acidified by 2 M sulfuric acid. The mixture formed a suspension which was filtered off and washed with water. The precipitate was dried in vacuo at 60° C. for 18 hours to yield 60 mg (0.11 mmol, 74.4%) of the analytically pure target compound.

Workup

  1. additionwere added dropwise
  2. customThe ice bath was remove
  3. customThe mixture formed a suspension which
  4. filtrationwas filtered off
  5. washwashed with water
  6. customThe precipitate was dried in vacuo at 60° C. for 18 hours
  7. customto yield 60 mg (0.11 mmol, 74.4%) of the analytically pure target compound

Sources & evidence

ORD record
ord-2d55f05624854e2ca6671b227c0e0165
Source dataset
uspto-grants-2016_02
Patent number
US09265763B2

Reaction notes

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