Aluminium lithium hydride → HCID 68461613, compound

HRID 2358739Notes

Reaction equation

HRID 2358739 reaction equation
[Cl:1][C:2]1[CH:16]=[CH:15][C:5]([O:6][C:7]2[CH:14]=[CH:13][C:10]([C:11]#[N:12])=[CH:9][CH:8]=2)=[C:4]([NH:17][C:18]2[C:27]3[C:22](=[N:23][C:24]([CH3:28])=[CH:25][CH:26]=3)[N:21]=[CH:20][CH:19]=2)[CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[NH2:12][CH2:11][C:10]1[CH:13]=[CH:14][C:7]([O:6][C:5]2[CH:15]=[CH:16][C:2]([Cl:1])=[CH:3][C:4]=2[NH:17][C:18]2[C:27]3[C:22](=[N:23][C:24]([CH3:28])=[CH:25][CH:26]=3)[N:21]=[CH:20][CH:19]=2)=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 68456171HCID 68456171, compound

Product 1

HCID 68461613HCID 68461613, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The product of Example 167c (88 mg, 0.175 mmol) was reacted with lithium aluminum hydride (13.3 mg, 0.351 mmol) in THF (5 mL) at 60° C. for 15 h giving the crude title compound which was purified by HPLC with TFA providing the product as the trifluoroacetic acid (15 mg, 14%). 1H NMR (300 MHz, DMSO-d6) δ ppm: 11.04 (s, 1 H) 8.92 (d, J=8.82 Hz, 1 H) 8.54 (d, J=6.99 Hz, 1 H) 8.18 (s, 2 H) 7.72-7.80 (m, 2 H) 7.59 (dd, J=9.01, 2.76 Hz, 1 H) 7.40 (d, J=8.82 Hz, 2 H) 6.99-7.12 (m, 3 H) 6.74 (d, J=6.99 Hz, 1 H) 3.97 (q, J=5.52 Hz, 2 H) 2.74 (s, 3 H); MS (ESI+) m/z 391 (M+H)+.

Sources & evidence

ORD record
ord-df9cdd36729e4e748e566e837608e587
Source dataset
uspto-grants-2010_07
Patent number
US07763731B2

Reaction notes

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