Diisobutylaluminum hydride → 7-Hydroxymethyl-4-(4-phenoxy-phenylamino)-pyrrolo[1,2-b]pyridazine-3-carbonitrile

HRID 1796648Notes

Reaction equation

HRID 1796648 reaction equation
C([O:3][C:4]([C:6]1[N:10]2[N:11]=[CH:12][C:13]([C:29]#[N:30])=[C:14]([NH:15][C:16]3[CH:21]=[CH:20][C:19]([O:22][C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)=[CH:18][CH:17]=3)[C:9]2=[CH:8][CH:7]=1)=O)C.CC(C[AlH]CC(C)C)C>C1COCC1>[OH:3][CH2:4][C:6]1[N:10]2[N:11]=[CH:12][C:13]([C:29]#[N:30])=[C:14]([NH:15][C:16]3[CH:21]=[CH:20][C:19]([O:22][C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)=[CH:18][CH:17]=3)[C:9]2=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 14487Diisobutylaluminum hydrideHCID 210250973-Cyano-4-(4-phenoxy-phenylamino)-pyrrolo[1,2-b]pyridazine-7-carboxylic acid ethyl ester

Product 1

HCID 221797297-Hydroxymethyl-4-(4-phenoxy-phenylamino)-pyrrolo[1,2-b]pyridazine-3-carbonitrileYield 64%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 406 (39.8 mg, 0.1 mmol) in THF (2 ml) was added DIBAL-H (1.0 M in CH2Cl2, 0.2 ml, 0.2 mmol) at −78° C. The reaction mixture was stirred at this temperature for 6 h, then at 0° C. for 2 h, quenched with water (0.1 ml). The solid was filtered off, and the filtrate was concentrated. The residue was purified by preparative TLC to give the title compound (22.8 mg, 64%) as a brown solid (2.5% MeOH—CH2Cl2). LCMS Found: (M+H)+=357.

Workup

  1. waitat 0° C. for 2 h
  2. customquenched with water (0.1 ml)
  3. filtrationThe solid was filtered off
  4. concentrationthe filtrate was concentrated
  5. customThe residue was purified by preparative TLC

Sources & evidence

ORD record
ord-96016a1daf224b03b46986ce7947f7f2
Source dataset
uspto-grants-2006_04
Patent number
US07030112B2

Reaction notes

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