Diisobutylaluminum hydride → HCID 57989626, compound

HRID 1671205Notes

Reaction equation

HRID 1671205 reaction equation
[C:1]([C:3]1[N:8]=[C:7]([C:9]2[S:13][C:12]([N:14]3[CH2:19][CH2:18][O:17][CH2:16][CH2:15]3)=[N:11][C:10]=2[C:20]2[C:21]([F:38])=[C:22]([NH:26][S:27]([C:30]3[CH:35]=[C:34]([F:36])[CH:33]=[CH:32][C:31]=3[F:37])(=[O:29])=[O:28])[CH:23]=[CH:24][CH:25]=2)[CH:6]=[CH:5][N:4]=1)#[N:2].CC(C[AlH]CC(C)C)C>ClCCl>[NH2:2][CH2:1][C:3]1[N:8]=[C:7]([C:9]2[S:13][C:12]([N:14]3[CH2:19][CH2:18][O:17][CH2:16][CH2:15]3)=[N:11][C:10]=2[C:20]2[C:21]([F:38])=[C:22]([NH:26][S:27]([C:30]3[CH:35]=[C:34]([F:36])[CH:33]=[CH:32][C:31]=3[F:37])(=[O:28])=[O:29])[CH:23]=[CH:24][CH:25]=2)[CH:6]=[CH:5][N:4]=1

Participants

4

Reactant 2

HCID 14487Diisobutylaluminum hydrideHCID 57989824HCID 57989824, compound

Product 1

HCID 57989626HCID 57989626, compoundYield 73.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of N-{3-[5-(2-cyano-4-pyrimidinyl)-2-(4-morpholinyl)-1,3-thiazol-4-yl]-2-fluorophenyl}-2,5-difluorobenzenesulfonamide (2.12 g, 3.80 mmol) in dichloromethane (DCM) (38.0 ml) at −78° C. was added DIBAL-H (18.98 ml, 18.98 mmol). The yellow suspension was slowly warmed to RT and stirred 1 hr. The reaction was quenched with Rochelle's salts and stirred about 1 hr. 4N HCl was added to clear the emulsion. The HCl solution was extracted with DCM (3×). The aqueous was passed through celite and neutralize with 6N NaOH. Solid formed during neutralizing and was filtered to obtain N-{3-[5-[2-(aminomethyl)-4-pyrimidinyl]-2-(4-morpholinyl)-1,3-thiazol-4-yl]-2-fluorophenyl}-2,5-difluorobenzenesulfonamide (1.57 g, 73%). MS (ESI): 563 [M+H]+.

Workup

  1. customThe reaction was quenched with Rochelle's salts
  2. stirringstirred about 1 hr
  3. addition4N HCl was added
  4. extractionThe HCl solution was extracted with DCM (3×)
  5. customSolid formed during neutralizing and
  6. filtrationwas filtered

Sources & evidence

ORD record
ord-08bfb6f8ece84b54b4ed393731fc3f33
Source dataset
uspto-grants-2011_08
Patent number
US07994185B2

Reaction notes

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