Aluminium lithium hydride → HCID 24784684, compound

HRID 1485355Notes

Reaction equation

HRID 1485355 reaction equation
[CH3:1][C:2]([C:8]1[CH:13]=[CH:12][C:11]([NH:14][C:15]2[C:25]3[CH2:24][CH2:23][N:22]([C:26]4[C:31]([C:32]([F:35])([F:34])[F:33])=[CH:30][CH:29]=[CH:28][N:27]=4)[CH2:21][CH2:20][C:19]=3[N:18]=[C:17]([CH:36]([CH3:38])[CH3:37])[N:16]=2)=[CH:10][CH:9]=1)([CH3:7])[C:3](OC)=[O:4].[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH3:7][C:2]([C:8]1[CH:13]=[CH:12][C:11]([NH:14][C:15]2[C:25]3[CH2:24][CH2:23][N:22]([C:26]4[C:31]([C:32]([F:33])([F:35])[F:34])=[CH:30][CH:29]=[CH:28][N:27]=4)[CH2:21][CH2:20][C:19]=3[N:18]=[C:17]([CH:36]([CH3:38])[CH3:37])[N:16]=2)=[CH:10][CH:9]=1)([CH3:1])[CH2:3][OH:4]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 24784681HCID 24784681, compound

Product 1

HCID 24784684HCID 24784684, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 2-methyl-2-[4-({2-(1-methylethyl)-7-[3-(trifluoromethyl)pyridin-2-yl]-6,7,8,9-tetrahydro-5H-pyrimido[4,5-d]azepin-4-yl}amino)phenyl]propanoate (Example 174, 73 mg, 0.14 mmol) in THF was added LiAlH4 (14.2 mg, 0.374 mmol). After stirring at rt for 4 h, the reaction mixture was quenched with satd. aq. Na2SO4. The reaction mixture was then filtered through a plug of diatomaceous earth and concentrated. The crude residue was purified (FCC) to give the title compound (45.4 mg, 66%). MS (ESI): mass calcd. for C27H32F3N5O, 499.26; m/z found, 500.3 [M+H]+. 1H NMR (CDCl3): 8.41-8.39 (m, 1H), 7.89 (dd, J=7.8, 1.8 Hz, 1H), 7.70-7.66 (m, 2H), 7.40-7.36 (m, 2H), 6.98-6.94 (m, 1H), 6.51 (s, 1H), 3.70-3.60 (m, 6H), 3.26-3.20 (m, 2H), 3.08-3.00 (m, 1H), 2.98-2.94 (m, 2H), 1.37 (s, 6H), 1.34 (d, 6.9 Hz, 6H).

Workup

  1. customthe reaction mixture was quenched with satd
  2. filtrationThe reaction mixture was then filtered through a plug of diatomaceous earth
  3. concentrationconcentrated
  4. customThe crude residue was purified (FCC)

Sources & evidence

ORD record
ord-bf5f48b852554c0ebf13b6d25c471a87
Source dataset
uspto-grants-2016_08
Patent number
US09422293B2

Reaction notes

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