Hydrochloric Acid → HCID 57928294, compound

HRID 1360184Notes

Reaction equation

HRID 1360184 reaction equation
[OH:1][C:2]12[CH2:11][CH:6]3[CH2:7][CH:8]([CH2:10][CH:4]([CH:5]3[NH:12][C:13]3[C:18]([C:19]#N)=[CH:17][N:16]=[C:15]4[NH:21][CH:22]=[CH:23][C:14]=34)[CH2:3]1)[CH2:9]2.[H-].C([Al+]CC(C)C)C(C)C.C1(C)C=CC=CC=1.Cl.[O:42]1CCCC1>>[OH:1][C:2]12[CH2:11][CH:6]3[CH2:7][CH:8]([CH2:10][CH:4]([CH:5]3[NH:12][C:13]3[C:18]([CH:19]=[O:42])=[CH:17][N:16]=[C:15]4[NH:21][CH:22]=[CH:23][C:14]=34)[CH2:3]1)[CH2:9]2

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 57928202HCID 57928202, compoundHCID 86583787Diisobutylaluminumhydride toluene

Product 1

HCID 57928294HCID 57928294, compound

Procedure

To a solution of 4-[(5-hydroxyadamantan-2-yl)amino]-1H-pyrrolo[2,3-b]pyridine-5-carbonitrile (150 mg) in tetrahydrofuran (3 ml) was added 1.01M diisobutylaluminum hydride/toluene solution (1.93 ml) at 778° C. The reaction solution was stirred for 18 hours under ambient temperature. To the reaction solution was added 1M hydrochloric acid under ice cooling, and the mixture was stirred for 30 minutes. The mixture was extracted with chloroform and washed with water. The organic layer was dried over magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure to obtain 4-[(5-hydroxyadamantan-2-yl)amino]-1H-pyrrolo[2,3-b]pyridine-5-carbaldehyde (100 mg) as a pale yellow amorphous substance.

Workup

  1. stirringthe mixture was stirred for 30 minutes
  2. extractionThe mixture was extracted with chloroform
  3. washwashed with water
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-0852e60595934d10a691882acb06a1a9
Source dataset
uspto-grants-2011_02
Patent number
US07879844B2

Reaction notes

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